First, some context. Over my work life I’ve pretty much always worked for technology companies. My first desk job was writing about the stock market for an online portal in the late 1990s (kids: ask your parents). Then I worked for three companies adapting their business to the Internet in different industries: travel and human relationships and advertising. My job in all three was to help these companies deal with the changes coming from the Internet and to help them capitalize on new opportunities.

I founded and ran my own startup and tried to make it work for 6 years. That didn’t take off and left me with some very valuable lessons and some annoying personal debts. Perhaps even in equal measures. So I worked in software to put my lessons to use and pay off my personal debts.

I’m taking you down this memory lane to say that I’ve always been pretty lucky to be pretty well paid, but that my pay was never typical. I had a salary and I had variable compensation (mostly stock options). I understood that the salary was to take care of daily expenses and the variable compensation was like lottery tickets — maybe highly valuable, far more likely worth nothing.

So I only really knew that two-part model of getting paid: salary plus options. And as I learned, especially with my own startup, the real upside could only happen in a place that really took off. When that lottery ticket got you a seat at a company that became a rocket ship. Let’s call this model of compensation the Tech Lottery Game.

Money Questions I’ll Avoid

The first thing that some people wonder but never get around to asking: How much money did we make from Slack?

Well, shoot, friend. That’s not something I’m going to spell out for you here. Sure we’re close after all these chapters, but we’re not that close. Sorry! It’s private to me and my family.

And really, what am I going to say? There’s no upside.

If it’s an amount you think is too much for someone to have, I might then be a rich and greedy asshole who should be doing more with their overweighted resources. And I probably should! If it’s less than you imagined I had earned, then maybe you think I should have done better. What a shmuck! Maybe you would have. And you probably would!

So maybe skip the rest of this chapter if a simple answer is all you were seeking. Math is just one way of describing the world, after all.

But if you’re still reading, here’s an invitation to think beyond the simple answer of a number because I think there’s so many more interesting topics around money to dig into, like playing the game.

Playing the Tech Lottery Game

You know the funny thing? At first, I didn’t realize that my work compensation was odd. It was the only model I knew: salary and options. Maybe some annual bonus mixed in. But that was it.

And I was pretty clueless about how to play to the Tech Lottery Game. I certainly didn’t rigorously analyze what companies might become rocket ships. I didn’t have any 5-factor ratings matrices. I took what I got.

But like any game, the more I played, the better I had a chance to get. And after I did my own startup, I inched along the gradient towards more mercenary, away from more missionary.

I started to think of the places I could work through the lens of the Tech Lottery Game. I had been trained to do so. That lens said, basically: make sure the cash situation all works and keeps everything going while really staying focused on the bigger picture, longer term value — options and ownership. That was the source of big value. And, since I was competitive and liked to win, and that was how the game got played, that’s how I started to play.

And I’m not alone. Pretty much everyone who works in tech is playing this game in SF, whether they admit it or not. Many fewer are playing it in a smaller place like Vancouver. It’s conservative and on the margin. Your parents and peers aren’t impressed by options. SF has way more reps at the game, a more mature understanding of payoffs and, as a result, a much more risk tolerant culture. Plus there are just way more options to compare.

So then the key question to play the game well becomes: what companies will be rocket ships?

When Slack came along, even if my first introduction was far before its first product in market and any success at all, I recognized it was a different proposition. How? The team, first of all. Their talent and capabilities and cohesion. Then their track record.

It was so different from what I’d experienced elsewhere it felt like I had almost been playing the wrong game. It was deeply different and that was why I was so keen to belong. Not for the money. For the chance to play the game at the highest level. I recognized the truth to the well-trod quote from Eric Schmidt to Sheryl Sandberg: “If you’re offered a seat on a rocket ship, don’t ask what seat. Just get on.”

But beyond picking the winners, what else can you look for to set yourself up to play well? Top teammates is #1. Another strong signal is top investors and an ability to raise money (or not need to raise money) that aligns with the company trajectory.

Then, what does the capitalization table look like? That’s the real code for the ownership of the company. I’m no expert on cap tables but I know a bit. Lift the hood on that spreadsheet and you can see so much. Here’s what I might watch for if I was looking.

• How many shares are there in the company? This will tell you what percentage of ownership your share options are proportionally.

• Who holds the shares? This will depend on the stage of maturity of the company. With maturity, the shares will tend to move from the company treasury to its stakeholders — mostly investors and employees.

• What are the liquidation preferences? This is how any sale of the company pays out its stakeholders, and the order of that process.

In general, I’d look for a simple and clean cap table that I could easily understand. One class of shares is far better as a employee to multiple classes or preferred shares whose holders get paid first. Any rachet or bonus / penalization clauses can be red flags.

Basically, what you’re seeing in the cap table and in the share structure are a reflection of power and control of the company. When a company needs investors’ money, those investors can force concessions on the company. When a company can choose its investors, it can make a much better deal for itself and its employees.

But your mileage may vary with all of this. You might know way more than me. You might not care at all about this. You might be well versed on vesting schedules and insider restrictions and tag-along, drag-along rights. Let me know if I got anything wrong here!

In 2020, I held stock in two companies that got acquired. Slack got acquired by Salesforce and Mobify (the company I worked at prior to Slack) got acquired by Salesforce. And though the acquirer of both companies was the same, the outcome was not. Slack was a $27.7-billion company with a clean cap table. Mobify was a snarl of a cap table with various liquidation preferences, squabbling shareholders and a few lawsuits.

And while that comparative experience certainly drove home for me how a similar outcome can have very different results, it’s a very limited sample size. What I’ve covered above are some basics I found helpful in the handful of places I’ve worked. The Tech Lottery Game is very complex. As an employee you may also play it a few times in your career.

Others in the game will have played dozens or hundreds of times. They will know the game very well. They will be deeply invested in the rules of the game.

Expect that the lawyers and bankers and investors and entrepreneurs will all know the game better than you. Find good folks you can trust and use their expertise to learn as much as you can. I hope that being knowledgeable about some basics of the game help you. They helped me.

World’s Smallest Violin

All the questions above, the requirement to understand the Tech Lottery Game and beyond, these are champagne problems, a terrific expression I learned from Bob Frati years before Taylor Swift sang about them. I’ll certainly take them and I’m certainly incredibly lucky to have them.

But you want to know something strange?

Growing up I always imagined I’d be someone who made a lot of money. I don’t know why, but I did. I didn’t know how I’d make any money (astronaut! hockey player!), but the idea held a powerful attraction for me, and I had no doubt it would come true.

My dad sold life insurance and my mom was a nurse. We were very middle class, in the suburbs, with a yard that backed onto a field. I had no reason to believe it, but I remember well a sense of certainty that I’d never had to worry about money at some stage in my life.

Maybe ever kid believes this?

Now many people are millionaires. I don’t mean this glibly. I mean it literally. In estimates, Wikipedia tells me there are 2,291,000 millionaires just in Canada. There are 24,480,000 millionaires in the US and 56-million globally. But those numbers are the easy part of talking about money.

The hardest part is still trying to answer the question of what makes a meaningful and fulfilling life. Money doesn’t answer that question for you. But it can provide the time, freedom and perspective to push on different options: family life, volunteering, community service, helping people, learning and travelling.

And most importantly, for me it has meant more chance to work on the relationships I have with people I care about. That’s by far the biggest luxury.

Money as MacGuffin

In fiction, a MacGuffin (sometimes McGuffin) is an object, device, or event that is necessary to the plot and the motivation of the characters, but insignificant, unimportant, or irrelevant in itself. The term was originated by Angus MacPhail for film, adopted by Alfred Hitchcock, and later extended to a similar device in other fiction.

– MacGuffin on Wikipedia

In technology startups money is the MacGuffin. It’s the thing we’re each meant to be on our individual quests to achieve. It’s our dragon-guarded treasure hoard. It’s the pot of gold at the end of the rainbow. It’s our holy grail.

Except. It’s not.

Sure, you may know you’re playing the Tech Lottery Game and it may definitely influence your decisions. But when you’re immersed in the quest, it’s not the point of the quest. And it’s not the payoff for the quest once you’ve reached the goal.

Do you believe that?

Maybe. Maybe you believe me. Maybe you don’t. Maybe I should be suspicious of myself and these assertions. It’s all pretty self serving to preserve my sense of being a normal Joe.

But as clearly as I can recall, in my experience at Slack and before, I never felt like I was on a quest seeking money. Yes, we were playing the Tech Lottery Game. Money could be a payoff for the risk of joining a startup, for our long hours and hard work and going above and beyond to try to make the thing take off like a rocket ship. We even stepped out of the day-to-day at times and it seemed like money could be in our future. It felt like a gauzy dream to glimpse on occasion. But it never acted as the motivator for any of those days.

The best motivator for the day-to-day work proved to be people — mostly teammates and customers. I wanted to do my best work for inspiring teammates who I saw also doing their best. I wanted to help our customers understand and then achieve the promise of what our product could do for them. I wanted to put my name on every job I did.

Showing up and doing our best, each day, made the work wonderful and worth doing. I’m not original in saying this. David Foster Wallace puts it this way in The Pale King:

Gentlemen, welcome to the world of reality—there is no audience. No one to applaud, to admire. No one to see you. Do you understand? Here is the truth—actual heroism receives no ovation, entertains no one. No one queues up to see it. No one is interested. True heroism is minutes, hours, weeks, year upon year of the quiet, precise, judicious exercise of probity and care—with no one there to see and cheer. This is the world.

I’m just lucky enough to have found a place that valued this approach, teammates who believed in it and a collection of people that put it into practice for my 7 years there (and beyond). I got to play the game at the highest levels.

We got paid and many of us did very well — far better than we had anticipated or expected at any stage of the journey. It was both a job and it was more. As I reflect on it all the words I return to are: What a lucky life.

But it’s over now. Like this story. That’s it. I hope you’ve enjoyed it. I hope it’s entertained you and given you new perspective. Maybe even one or two things you can find useful for your own life.

It’s been my pleasure to think about it and write it and narrate it. Thank you for coming along for the ride.

— JS, March 18, 2026

PS: Here’s my final request of your time. If you haven’t yet, please take 1 minute and tell me what you’d like to see next from A Slack Story. Thank you!

But I suppose there is a bit more. Some questions that remain. Here are the top three that strike me as worth exploring. They proved consequential to the story but haven’t really been unpacked.

1. Thinking about luck — How much influence luck played in Slack’s journey and my own journey at Slack.

2. Culture vs People — How much of Slack’s success resulted from the people hired or the culture they operated in.

3. Leaving before it’s time — How I thought about leaving Slack and building up a life to head to, not just one to leave.

I had another question in there about money and MacGuffins that I’ll tackle in the next chapter. Turns out, it’s a bit bigger and needs more unpacking.

And what about you? Any questions you’d like unpacked? Leave a comment below or email me direct: sherrett@gmail.com.

Thinking About Luck

Sure, I think about it. But I struggle with this question sometimes because the answer is so unknowable. How much of Slack’s success depended on luck? How much of my personal success depended on luck? Unknowable. But also, a lot, I’d say.

From Michael Lewis’ Princeton 2012 Baccalaureate speech:

“This isn’t just false humility. It’s false humility with a point. My case illustrates how success is always rationalized. People really don’t like to hear success explained away as luck. Especially successful people. As they age and succeed, people feel their success was somehow inevitable. They don’t want to acknowledge the role played by accident in their lives. There is a reason for this. The world doesn’t want to acknowledge it either.”

...

“Don’t be deceived by life’s outcomes. Life’s outcomes have a huge amount of luck baked into them. Above all recognize that if you’ve had success you’ve also had luck. And with luck comes obligation. You owe a debt. And not just to your gods. You owe a debt to the unlucky.”

Slack launched at just the right time to meet its market, at just the right time to have its market pull the product out of the team. Yes, Slack did all the things Slack could do to maximize its probabilities of success — great product, opinionated positioning, terrific public relations. All the pieces worked together in harmony.

Internet Relay Chat (IRC) sowed the seeds of Slack’s success by establishing much of the product model and conventions early Slack relied on. Web and mobile technology had advanced so a freemium trial model could work. Billions of people had an Internet connection. I could go on and on with factors that affected our success and proved essential.

Slack just basically appeared in the world at the right moment for a chance to succeed. If Slack launched a year earlier or later would it have succeeded to the same extent? I think it’s impossible to know but it’s also unlikely. It just hit right.

And in the same way that Slack appeared in the world at the right moment, I appeared at Slack at the right moment for me to have a chance to succeed. I got the contact from Rebecca to have the coffee with Stewart that led to my first job. I found valuable work within the scope of that first job to get to please sit next to the money, and that led to my second job, and then again my third and fourth and fifth jobs.

I never really knew where I was headed. My career isn’t a template for anyone to follow. If anything, it taught me to let go of the vanity that I had control over my direction. I did have some influence, but only some.

When I coach kids sports now I can see they often get frustrated or elated by things that happen in the game. An official’s call benefits them. A bounce leads to a goal against them. The outcomes big and small can be tipped one way or another by chance. The world has plenty of randomness in it.

In the face of that randomness, I try to get them to see the luck, acknowledge its role, then focus on just the things they can control: their effort, their attitude. They have 100% influence over those two things and no one else can do those things for them.

Then once they have ownership over their effort and their attitude, I ask them to own their part of their relationships — with coaches, with the other players, with themselves and with their parents too. Again, no one else can do this for them.

This isn’t a perfect model of how to operate in a world where luck continues to influence us. You still have to be able to see opportunities and be brave to try to seize them. You still have to be aware of probabilities and situations — when to push your luck and when to sit back. But I find it’s a good start.

And once you start to do these basics it’s amazing how luck can take care of itself.

Which Drove Which: Culture vs People?

The tendency with our first questions seems to be to assume it’s a zero-sum problem. People say things like, Slack’s success was 50% luck and 50% controllable aspects. The higher the perceived influence of luck, the lower the perceived influence of talent or hard work or smarts or jellybeans.

I won’t quibble with that here. Read the above section and you can see I think it’s not really a question worth spending a ton of time answering, if it’s answerable at all.

But I will strongly argue that the question of culture vs people is not a zero-sum question. It can’t be reduced to 50% culture and 50% people because each aspect of the opposition reinforced and drove the other. A better culture meant better people meant a better culture, and on and on.

So how much of Slack’s culture’s success was hiring the right people? Lots. How much was giving those people permission to be their best selves? Lots again. How much was the luxuries and freedoms we enjoyed — time, money, momentum — that acted as tailwinds? Bingo, bingo. Those all pushed us ahead too.

If you want to hire the best people, build the best culture. If you want to build the best culture, hire the best people. And, like planting a tree, the best time to do it was long ago, the next best time is right now.

Just think of your own career and how you’ve done varying levels of work in different cultures. Sometimes better. Sometimes not as good. You changed what you brought to the work and the work changed you. It was my experience that the people drive the culture AND the culture drives the people. It’s a bunch of complex and interacting systems that are somewhat opaque to their participants.

To put it into more concrete terms, ~80% of Slack’s investments every year (like almost all software companies) were in people: salaries and bonuses and benefits and desks and programs, etc. The biggest thing we spent money on was by far people. Like Soylent Green, Slack is made of people.

And consistently we saw that the top source of excellent new people joining Slack came from referrals from excellent existing employees. That virtuous cycle got started early and never in my time at Slack petered out. It didn’t depend on any cash kickbacks. It depended on Slack being an excellent place to work where people wanted to pull in more excellent people to work with. There was reputational contagion.

So it started with the people and they created the largest return on investment. And the people built the culture. Then the culture attracted additional people, who built new variations on the culture, that attracted more terrific people. There was no either culture / or people. It had to be both. And on and on. Chicken and egg.

Leaving Before It’s Time

Did I leave at the right time? Seven years and five jobs after I started? Maybe.

If I think of the through line of my work at Slack, I wonder: was my job consistently to be invisible and yet probing? To be the person doing marketing when we didn’t do any Marketing. To be the person doing sales before we had Sales. To help do a job and to be available to do new things when I found an adjacent space that needed something done? Partially, I think so. Or that’s how I found my belonging and created value.

At some point around 2018 I remember Stewart telling us that our opportunity was to be an N of 1 company — a Google or a Salesforce. We had the chance to create and own a large and growing market that touched a global audience. That was the size of the ambition we could reach. We could create a new digital way for people to communicate and work together. We were trending to be 2,000+ people. We went public. We crossed the $1-billion threshold of revenues.

Yet I found I was less excited about these goals and achievements. What did it mean to be an N of 1 company? We already were a verb in the vernacular.

The story I didn’t tell you about almost getting PIP’d in January, 2020 is that I was feeling pretty lackadaisical and doing a lot of questioning of my direction. If I no longer had to work for money, what did I work for?

I had to find new challenges to be excited about. I drew up a list of what I wanted to do and those challenges ended up being mostly outside of Slack. I used that list to create a portfolio of things to aim towards. I wanted to learn to play drums. I wanted to learn to fish on the ocean. I wanted to contribute to a better planet. I wanted to help people in my community. I wanted to be home with my family and not travelling.

I remember my last trip to SF in February, 2020, right before the COVID pandemic really ramped up. From seat 13F on the flight I watched the runway shrink below me. We crossed the water of Georgia Straight where the milky plume of the Fraser River lingered above the deeper saltwater. We climbed away from the forests and islands and reflecting water and all the places I actually wanted to be, and I knew I had to make a change.

That moment sticks with me as one of a few small realizations that I had to move on, and I had to leave before I was ready. Time ticked. Life passed and I had run out of spaces at Slack where I could be invisible yet probing. I had to jump into ambiguity, into seeing what I could do in a new life.

On that last trip I felt like I was saying goodbye to San Francisco, goodbye to that life, goodbye to Slack, goodbye to the person I had been.

One evening of golden sunshine I rode an electric-assist bike down Market Street with my teammate Chapman. We went to the Zuni Cafe and ate the bread and chicken salad I had heard of but never tasted. It was glorious and like my farewell dinner.

A week later travel shut down. Offices closed. We started disinfecting groceries before unpacking them and I started to build my plan for life after Slack.

Up next: Money as MacGuffin — Money can change things. Mixing with friends and family and kids. World’s smallest violin.

Lover don’t be sad
Think of the time we’ve had
The moment’s truer, now
It won’t last

— Amerika, Wintersleep

My last day at Slack was June 5, 2020, exactly seven years from my first day.

When I joined, Slack had been 8 employees in 2 offices. When I left, Slack had well over 2,200 employees in 16 offices worldwide. When I joined, Slack had $0 in revenue. When I left, Slack was closing in on $1-billion in revenue.

Where no one had heard of Slack when I joined, including me. When I left, WORK was a public stock on the NYSE worth billions of dollars. Slack was as close to being a household name as a business-to-business software company could be.

Things had changed.

Slack came up in daily conversations. Slack lived beyond Slack, outside of Slack. “I slacked it to you,” I heard people say. “Slack me that file.”

Every time I saw someone using Slack in a coffee shop or on a bus or train or waiting in a lobby it remained a small thrill. Hey, I worked on that product! That familiar knock-brush sound always felt like a delightful smile in audio form.

So much meaning felt compressed into Slack for me. That simple messaging system. That simple way of connecting. And I was leaving it behind.

Leaving After 7 Years

I joined Slack to belong to a team made of amazing people who worked to create a product that positively affected how its customers worked. That seemed accomplished far beyond any hallucination of our wildest dreams, a daily reminder of pinch-me moments.

I decided to leave Slack to start a new part of my life. And that was a hard decision. I still really enjoyed working with my teammates. The people I was lucky enough to work with were a pleasure every single day. They challenged me and inspired me to do my best work. That was basically the problem.

Was I ready to leave? Not really. Working at Slack continued to prove so absorbing that all the other things I wanted to do in my life came second. And, knowing myself, I knew I was lousy at doing multiple things at once. So I had to leave.

I was 44 years old. Statistically, likely more than halfway through my time on the planet. If I really wanted to get to all the other things I wanted to do in life, I had to promote them to my top priorities. I had to subtract the work that absorbed the top priority. I had to leave Slack to move ahead.

I decided to leave Slack a few months before I actually left. I told only my wife. I wanted to leave exactly 7 years after I’d started. I once heard a numerologist say people’s lives happen in 7-year cycles. That seemed like good symmetry. Then the COVID pandemic changed how we worked at Slack. It made it harder to leave because everything held more uncertainty. But I still knew I had to leave to get started on the rest of my life.

I wanted to leave on top and that meant leaving before I was ready. And I wanted to leave something behind as a testament to the people I had worked with, to thank them.

Below is a shortened version on the document I left behind titled Thank You, Slack. If you’ve been along for all of A Slack Story, you might hear some echoes.

What I’m Leaving Behind

Dear Slack,

TL;DR If you’re reading this: Thank you. Working here at Slack has been the best work of my life — the most rewarding, the most enjoyable, the most challenging. It’s been the best kind of fun: hard fun. It’s been an amazing ride. It would certainly have struck anyone as delusional dreaming should I have told them about it at the outset. In short: it’s been way beyond expectations and it’s been a privilege. Thank you.

Friday, June 5, is my last day at Slack. That will be exactly 7 years since I first started working on Slack, as the ninth team member, after having coffee with Stewart on the patio of JJ Bean in Vancouver.

I’ve tried to be tight with the stories below. Perhaps 20+ GoogleDoc pages contradicts that intention. Perhaps not. In short: we did quite a few things and they seemed worth sharing.

In the sharing, I know I’ve missed some stories and (more importantly) some people. Please know that everyone I have worked with here at Slack has been important to me. Thank you: I will miss you all.

Marketing Consulting

That’s what the proposal I sent to Stewart after our coffee meeting said. So that’s how I started working at Slack — what was our market? What was our product? What competed with our product? Who were we?

It was June, 2013, and there was both too much to do — Slack competed with every way people worked together and there was no budget for it as a product — and not too much to do — our team had a very clear identity for themselves, had worked together for cumulative decades and were pretty darn good at product and marketing and getting attention. So where should I get started?

I flew to San Francisco to the office on Clementina for a one-day session to get to know the team. There was a parachute covering the skylights because it was too hot. The kitchen tables were unusual and I later learned they were from a morgue.

I hardly remember what we talked about but all the marketing strategies that I knew worked from my Business Software Marketing playbook days seemed slightly hackneyed. These cool kids had built a video game. Now they were asking me to help them figure out how to speak Business? E-books for IT decision makers and gated white papers on dedicated landing pages and contributed articles to Harvard Business Review seemed pretty lame.

So we started on positioning. How would we tell people about this new product that solved a problem they felt like they knew they had but it wasn’t their job to solve? What was the clear and compelling reason to give a shit about something weirdly named Slack?

Maybe it was a scalable infinite brain. Time to communicate better. Making better decisions, faster. For teams of 5 to 150 we were pretty sure we could kill 75% of their email in 3 days. We were also pretty sure that collaboration doesn’t come from software.

Five of our ideas ended up being landing pages with specific positioning that we drove traffic to, tested and then measured how people responded. Did they sign up to learn more? In the end, we decided (though the absolute data told us an unclear story) what people wanted was to Be less busy.

On August 12, 2013, we launched a single-page website with nothing to do except sign up and get an invitation to try a new product. It held a simple promise: Be less busy.

8,000 people signed up in the first 24 hours and 16,000 signed up by the end of that week. It seemed we were on to something. All the sign ups got piped into the #leads channel and we combed through them for gems: Walmart Labs, Boston Consulting Group, AOL, MIT, Deloitte. Sometimes we chirped them a bit.

On a personal note, I saw for the first time how PR could drive attention and results on a scale I had never seen. This wasn’t tactical, IT-only press relations. This was mainstream, big time PR. If Silicon Valley was like a large royal court (and it is), with kings and jesters and (not enough) queens, we had a prince and he was well known and what he said had an automatic audience. We ran with it.

Now that we had some ‘customers,’ someone had to speak with them. That seemed like a good next place to concentrate my efforts, so I started inviting customers to try the product, then emailing and calling them for feedback. This was partially marketing, partially sales and partially support. The initiative called Everyone Does Support started because everyone actually needed to do support.

I got my feet wet demoing the product as Stewart’s sidekick and then he got too busy so the demo job fell to me. This pattern repeated itself many times.

Gradually from my conversations, some customers’ patterns began to emerge:

• Everyone had some cobbled together communication / collaboration “system” that no one had decided on in any concerted way yet everyone had to use.

• Everyone had to use a part or the whole of the system and felt the pain and frustration of using it to get their work done.

• It was no one’s job to fix the system. No one had decided on it. No one had a budget for it. IT paid for parts of it (email, active directory, ESNs).

• Email was the base system. Everyone was on email from their first day at the organization because it was tied to their corporate sign-in identity.

• Some IM or chat products were added on to the email or phone systems (Skype, Lync, Jabber) as vestigial organs.

• Many teams were also free to add on their own parts to the system, so products like HipChat, FlowDocks and Campfire sprung up for technical and creative teams.

• No one was happy with how they were communicating.

This was the context we were taking Slack to market in. We had to figure out how to make something better, and to convince a minimum of ~5 people to try it, consistently, together, for more than a day or two. As we said at the time, Slack is a terrible single-player experience, so we had to synchronize all ~5 of the people trying Slack to get over the Suck Hump™.

Going back to read those early customer development interviews with Beyond the Rack, Lonely Planet, Hootsuite, it’s apparent we were talking to the right people and getting good information from them because we were genuinely finding an underserved need.

And, tell me if this all sounds familiar too. From one of those interviews:

Sandy is a product manager and a director of IT for the company. When she first heard about Slack her ears perked up because of the cut down in conversational emails – the ones with just ‘Okay.’, the ones where people reply to the wrong version of an email.

This past weekend they used Slack how they wanted to — to do a major server migration. They created a private group to coordinate it and it worked really well. She is their internal advocate and has buy-in from development and support and QA and IT. Those groups are really enjoying using Slack.

They’re having a little more challenge with getting buy-in from sales and management. She has a couple of people with hybrid roles who are a less technical audience who she sees as her go-between to the laggards and her test audience.

JS: What barriers do the sales and management folks see to Slack?

They have to keep it open. She tried to get them to use the app but it didn’t work for them. People said to her that it was additive — that they had to have IM plus this plus email open. She has tried telling them that Slack replaces IM and most of their email but there is resistance.

Zoom ahead 7 years from the day of that interview and we’re having a very similar conversation with a later-adopting customer. That’s how big the market for Slack is. Wow!

We were getting traction and people — once they got over the Suck Hump™ — were using the product and using it a lot.

We rolled through the invitations people had signed up to receive and ramped up invites to 50 / day, 100 / day, 200 / day. The product was getting better all the time — the rough edges sanded off and the gaps filled in. As a continual quest for us to consider, I remember Stewart asked the team: How can we maximize the surface area of the company to customer feedback?

Twitter took off for us. Customers had questions. Customers had complaints. Customers also loved the product and started proposing marriage to Slackbot. We collected 20+ proposal in the first few months. That was surprising.

We created a Wall of Love on Twitter with an end-of-life feature designed to collect a maximum of 2,000 tweets in a list. We poured the tweets in and pointed prospective customers to the link: See? People love Slack! We had to create a Wall of Love 2.

There was still too much to do and every night I went home and told my wife that the work was great and there was so much of it to do and both were true!

Saying No Nicely

To cope, we had to evolve. I started discovering the privilege of saying No to things. People pitched us things all the time and it was a joy to say No. It was incredibly liberating to say No because it meant I had the space to focus on just a few big things.

I started to see that from a product perspective, saying No was essential. Slack was an argument for a way of working in the world. Each feature added or (better!) not added was part of that conversation. The more features, the more that had to be held in memory to stay current on the argument we were making.

In the customer-facing world, I saw our product folks saying No and wanted in on the clarifying simplicity it provided. In my role, setting up a call could be a 3 to 6 email correspondence that sucked for all concerned. So I tried to put all the information and options into single message. I tried to change the context.

“Do you want to do a call?” (which inevitably was greeted with silence — our customers’ version of No) became:

Here are 3 times that work for me to do a call:

• date / time 1 (your time zone / my time zone)

• date / time 2 (your time zone / my time zone)

• date / time 3 (your time zone / my time zone)

If none of those times works for you, please suggest a time and we’ll work to make it happen.

Once we have a time, I’ll send you a calendar invite with the meeting details and a video / voice conference link.

Everyone could choose a starting time. It was way easier than deciding if they wanted to do a call or not.

I started to treat emails as landing page copy designed to get a specific response. Subjects were the headlines. Bullets were your friend for scanning. Always start with a thank you, even if it’s just to thank them for continuing the conversation and sharing their feedback.

Saying No Nicely meant we got to spend more time, energy and emotion on the core things that really mattered, and I truly believe that mattered then as it matters now.

More Holey Moley

In the midst of trying to keep our collective heads above water we started to talk about the kind of organization we imagined. Now that it seemed Slack was going to be something, what did we want it to be?

A sign that said More Holey Moley went up above the door of the office. Stewart told a story about doing the best work of your life. We talked about Four Seasons’ mission statement based on The Golden Rule: To treat others as we’d wish to be treated ourselves. We shared the Disney blog post, What time is the 3 o’clock parade?, so we could start thinking more broadly about what our customers needed and how we could meet them where they needed help (and lead them, even).

I bought us a sign for the entrance to our office.

We were still pretty overwhelmed but we knew we were building something people cared about and that affected people. That was really inspiring.

We started hiring folks (or rehiring with many great people returning from Glitch). People I was talking to asked for a one pager to show to their boss, so I wrote a one pager with a pun in the title: Time to Communicate Better.

I used three classic Hemingway quotes to keep myself focused every day:

• Never mistake motion for action.

• The shortest answer is doing the thing.

• The best way to find out if you can trust somebody is to trust them.

At the end of 2013 I went for a walk with Stewart around the seawall in Vancouver. He said to me: “That thing you’re doing working with customers, I want that to be the only thing you do. We’ll call it account management.”

“Okay,” I said and we were off to the races.

Account Management

We had a target date set for our commercial product launch: February 12, 2014. Then, we’d really see what we had. Would people be willing to pay for Slack?

I’ll not belabour the question: yes, people were willing to pay for Slack. Right away, too. There was a queue. This is what Stats Time looked like on launch day.

At the start we gave customers credits to pay for Slack, or some of Slack. Just for using Slack! $100. $250. $50. There were experiments run.

We gave away credits like they were free. Like virtual money collaboration fairies we sprinkled them on accounts and then told the accounts about them to see if they were interested in trying the paid product. Really, they were just deferred revenue.

We even let customers earn their own credits through the Give 100 / Get 100 referral program. The credits were a terrific nudge wherever there was underlying usage and value in the product. People signed up.

And we didn’t discount the base price. When people wanted a better price for upgrading all 80 users at a company (I remember you, Saucelabs), we negotiated with credits. When they wanted to be invoiced for their payment instead of paying by credit card, I created an invoice template in Word on my desktop and output a PDF. When they were ready to pay, I created a Bug in our homegrown Bug Tracking System, assigned it to Myles or Cal and they did the backend upgrade thing.

A few days before we launched the paid product we knew we had lots of teams that wanted to upgrade. One of the largest was Walmart Labs who had ~3,000 users registered on Slack but with only ~1,100 active users. If they were going to upgrade, some admin would have to go through and deactivate ~1,900 users so they didn’t get billed for all of them. That seemed like a shitty task, so Cal wrote the code to check for active users and then only bill the customer for those active users. We wiggled around the active user rules to get them mostly right, and then launched the code to coincide with the product launch.

Over the next few months I must have explained how our active user rules worked 100+ times. People loved it, but they were also confused. It removed risk for them and let us say, “If a user doesn’t use Slack, we won’t charge you for them.” I started calling it the Fair Billing Policy because it made it sound fair and official and like it wasn’t up for debate. So that became the name.

We were in business now. We got a CFO and I started reporting to Allen Shim. We did an offsite in Sonoma where I met in-person many of the folks I had been working intensely with for months. They were good people. Ben Jenkins had a quadcopter drone that rose above the grass, above the roofline of the hotel, above the water tower of the Fairmont Sonoma, almost out of sight, shooting a video at golden hour that was so crisp and clear it could have been in an IMAX film. Banjos and guitars and ukeleles came out later.

We got around to doing something about swag. We had talked about socks and now we were making them. Cory designed a great pattern for a Slack tartan and I figured out getting them made. People liked the Slack socks whose first version of 250 pairs was similar and yet not similar to their second version, and whose second version with their custom-dyed yarn and custom weave went on to get replicated many tens of thousands of times. Maybe 500,000+ pairs are out there now?

We aspired to an experience of sprezzatura for our customers, as they say in Italy. We raised some money and everything rushed ahead in the blurring reality of the doing of the business.

So yeah, we tried Slack

We started some promotion to tell people about Slack. Sandwich Video was the hot thing. So hot, in fact, that Stewart’s original outreach to them was met with crickets.

Eventually, we got in touch with them. Adam Lisogor came to meet with us. We worked out a script that was both funny and topical. It had some character while also following the standard product intro video format — introduce a problem and what’s at stake, insert product as solution, resolve the tension of the problem with how much better the world is now with (product).

We watched the video final cut in our office with Adam. It was great. But it had no title. We watched it again. In the silence that followed I quoted the video, “So yeah, we tried Slack.” and we had our title. (Amazingly, the sequel is really terrific – Sandwich works from home – in Slack.)

The business rushed onwards and onwards. We got to $10-million in ARR by October of 2014 and ran a report to find that ~70% of people signing up never got in contact with anyone at Slack. They came to Slack.com, signed up, tried the product, invited folks to try it with them and upgraded. Yay!

For the balance of folks, they needed help with Slack. They needed to understand what it could do for them, how it fit into their day, and how they might use it. Those were the people I worked with.

Within that ~30% of upgrades we touched, about half needed 1-3 touches. They had quick questions or simple processes to upgrade. The other half needed 20+ touches to upgrade. These were the characteristics of Enterprise customers and we could see it in the barbell distribution of contact points. We had to hire people to help the Enterprise.

So we did: Account Managers. Kim Graves joined in Vancouver. We pulled my desk away from the wall and she sat on one end and I sat on the other. Accounts team: activate! AJ Tennant joined in SF and flew to Vancouver to meet our fledgling gang. We made room for him on the same desk. He sat on a box and we made it work.

People with sales experience started to apply and to teach us in their interview (they had to demo Slack to us if they got to the final stage) better ways to sell our own product. That was a surefire indicator they were solid candidates. Dave Macnee joined. Christina Meng joined. Mike Clapson joined. Kyle Shackley joined. Maggie Hott worked for Eventbrite in SF and came to Vancouver for her customer Lululemon. I met her in the same JJ Bean I had met Stewart at 16 months earlier and she had a bag of Ghiradelli chocolates for our team. Maggie joined.

We created a scorecard for what we were seeking in candidates and scored them on Communication, Culture, Trust, Poise, Savvy and Grit. That seemed like a good framework. Certainly better than nothing and better than anything else we were using before.

The business continued to rush onwards and onwards. We started to get more inquiries from all over the world. Doing calls at 5 am was a bit of a pain. Expansion was in the cards and someone had to go to do it.

My wife and I had always wanted to live and work internationally, so we signed up to move to Dublin to open Slack EMEA.

Slack EMEA in Dublin

I moved to Dublin in April, 2015, with my wife and our son to start the Slack office. Dublin was growing and US-tech companies were a major driver. We had 3 people at Slack Dublin to start: me, Hanni and Aaron. We set up in a co-working space in the Guinness Storehouse beside the space Etsy had just vacated for a bigger office.

A pretty specific process existed for US-tech companies to set up in Dublin and we plugged right in.

• Start the first office and focus on sales and customer service teams. Grow to a few dozen folks.

• Get your second office, expand the sales and customer service teams and add representative business services: finance, HR, accounting, office management.

• Start to develop specific market expertises for your top countries / regions.

Google had ~3500 employees. Facebook had ~2000. LinkedIn had ~1800.

Having that template proved helpful because everyone we worked with was well versed in it. Service providers for payroll, legal, accounting and so on knew the process. Recruiters knew the process. Candidates knew the process. We were a startup on the scene and we had to find our place accordingly.

First up, we had to tell people we had opened the office. We joined the Irish American Chamber of Commerce and that right there is a serious business network. We launched Slack Dublin in the Long Library at Trinity University with the Irish Taoiseach (Prime Minister, pronounced “tea-shock”) and prominent ministers.

We had to start again with the basics — tell the world we existed, why our product mattered, what it did for our customers, what we were arguing should be different about the world of work. People were skeptical too. Were we like a Facebook for businesses? Were we a product for developers? Or just for startups? The context they were trying to fit Slack into was new and different.

For me, the day to day was also like a step back in time to the original Slack YVR office. We had no plumbing or kitchen in the office. Getting a fridge into the office deserved a celebration. Bathrooms were common to all the offices in the building and an adventure to get there and back — a minimum 4-minute round trip, in case you were booked in back-to-back meetings.

On the upside, the journey to the bathrooms did mean you walked over a lovely Guinness toucan mosaic.

Each day felt like a struggle to find the right thing to work on because we were lucky enough to have so many things to work on. We were starting fresh in building the business with a huge support crew, strong reputation and customer traction. Significant tailwinds.

Our team was still called the Accounts team and we had one role to hire for — account manager — and we were hiring as quickly as we could. Successful candidates were expected to be the single point of contact for a customer, able to do a technical demo, answer a security questionnaire, negotiate a contract and do discovery, for starters. Candidate interviews often happened walking the cobbled streets of The Liberties and horses and horse carriages were common. Watch your step!

Again, the experience in memory is a blur. I tried to walk a different route to work each day to see the city. I learned each working day had to be parcelled out into time zones: first thing in the morning for the local Dublin team, midday to prepare for the Americas team, late day for meetings with HQ.

Stewart visited and hosted an All Hands from the Dublin office lounge that we called The Snug. He also rode, Back to the Future style, in a DeLorean with Davina.

We were building something and learning what we needed to build at the same time.

Starting a Culture

We started from pretty much a blank canvas to create what we thought could be Slack’s culture in Dublin and Europe. We had the mission statement and the 6 values but we didn’t know what a new office had to do because we’d never opened a new office like this — in a new culture and continent.

What would be the same as Slack’s global culture? What would be unique to Dublin and Europe? It was a consistent question and I’m not sure it’s even settled today — there’s just the guidance of more past decisions to point to.

The most important parts of the culture were the people we hired, and on that front we were incredibly fortunate. To be clearer: I was incredibly fortunate.

Paul Murray was dogged after customers. Alia Lamaadar joined the team with her tenacity and her name was 60% As. Alison joined. Bernie joined. Panos joined. Julian joined. Each brought an incredible willingness to learn and push us ahead — to be flexible and adaptive and to put customers first.

I had to learn how hiring in Dublin was different too. The questions I had asked in US and Canadian interviews got a very different answer. For example, “Tell me about a time you had to lie at work” shocked people so much they were unable to answer. Candidates held back telling their stories. We started scheduling longer interviews so they could get comfortable with the process and settle in to tell their story. They had to feel safe to shine.

We tried to strike a balance on what we carried over and what we created. We celebrated global Slack traditions like Caloween. We created new local traditions like Small Hands.

On the business front, we ran to talk about our business wherever we had the chance. “EMEA: Europe, Middle East, Africa” revealed itself as a construct for convenience. There was no EMEA to the outside world. That’s just how we (and every other US tech company) talked about it. Even the EU was incredibly diverse with 27 member countries and 24 official languages.

The fun with acronyms didn’t end there either. The way software companies parcelled up EMEA revealed itself as we built the business: DACH was Germany, Austria and Switzerland, Benelux was Belgium, Netherlands and Luxembourg; the Nordics were Norway, Sweden, Finlay and Denmark; MENA was Middle East and North Africa. It was a big, big world.

Customers and chances to tell the world about Slack took me to London, Copenhagen, Oslo, Cardiff, Madrid, Frankfurt, Berlin, Amsterdam, St. Andrews, Edinburgh and beyond. London, London, London. As a bonus, I was sometimes lucky enough that my family came along and we made a long weekend of it — cycling on Copenhagen’s paths, hiking in Scotland, swimming the Oslo harbor.

We pressed on to spread the word. There was a terrorist attack in Paris and Hanni (who led our customer experience team and spoke passable French) and I were off there the following day to pitch to LVMH. The high streets around the Champs Elysée were lit up for the Christmas holidays, expecting throngs of shoppers, yet empty and yawning.

We grew the teams and filled our starter space and moved to a shiny new Dublin office in the same building and neighbourhood as companies we’d grown to be considered peers with — Dropbox and Twitter. We were following the process. We were building the business. We were telling jokes. Did you know Ciaran ran a marathon?

Other global changes happened around the same time. On the first Accounts Sales Team Offsite we became the Sales team (thank you for hanging with us Success until you got top billing too). We opened in Melbourne, Australia. We started to hire in London and planned an office. Rav started before the office opened, so he always claimed his dining room table as the first Slack London office. Bob Frati started as our new global leader.

In Dublin, I started to look for someone to take over Slack’s sales leadership in EMEA. Many Dublin coffee shops saw my face. We weren’t in a hurry but we weren’t slow either. Bob visited for a week and we interviewed candidates together in Dublin and in London. We were also looking for a sales leader for the UK. Our appetite for excellent candidates was insatiable. We found folks and needed more.

Phil started in Dublin to lead the SMB sales team and it was a huge help to me. We signed up key EMEA accounts like Schibsted, Deutsche Borse, Adidas, Spotify, Financial Times, Daimler, Paddy Power. We crossed $10-million in ARR as a region. Stuart started to lead our UK team. We moved to a new London office. Johann started to lead our EMEA team. A global sales team started to take shape with all the Enterprise Software rigour needed to continue to propel the business.

It was early 2017 and Dublin didn’t need two sales leaders. What was I going to do next? I wanted to have an impact and work with customers. I had to find something new to do.

When I look back at my time in Dublin I keep coming back to the first All Hands hosted by Stewart from there. He asked me what was the best thing about our work and the answer was simple: The people. It’s the people in Dublin that I miss the most and will continue to miss the most. I miss you folks!

Executive Programs?

At the beginning, I confess, I had no idea Executive Programs and EBCs (Executive Briefing Centers) even existed. Then, the more I learned, the more interesting it became as a place to have an impact and continue to tell Slack’s story. I joined up even before I left Dublin.

Each briefing we ran was a mini production. I loved working both behind the scenes to enable and coach others to be the stars and role players, and occasionally doing some on-stage work myself. We parachuted into an account, learned as much as we could as quickly as possible, packaged that up for all the people who needed to be involved, and helped to run the show. Then we gathered feedback and exfiltrated to run the next briefing.

We started with one EBC in SF and expanded to three others in Tokyo, NYC and London. We started doing a few dozen briefings a year and grew that so in 2019 we did over 500 briefings. After crunching the numbers we learned that doing an EBC with an account improved the close rate of an opportunity from 33% to 77%. That seemed very good.

“Innovation Tours”

We also started getting asked to host “Innovation Tours.” These were groups of folks travelling to Silicon Valley (and some to Dublin or NYC as well) to learn from leading companies.

These Innovation Tours seemed like (a) something we could do well and (b) something that would introduce Slack to new people. And since no one stopped us from doing them, we started hosting them just to see what could happen.

Here was a whole other industry I had no idea existed until I was ingrained in it. People started visiting Slack in Innovation Tour groups from France, Germany, Sweden, United Kingdom, Thailand, Japan, Australia, New Zealand and beyond. They loved to hear the Slack story, to tour our offices and get a glimpse of the insides of a world-class technology company. That was us.

As we kept doing Innovation Tours we discovered there were 3 main types of groups and they were roughly (business wise) in this order of value:

1. Companies sending their execs on a learning retreat — the C-suite of ThyssenKrupp, the international country GMs from Thomson Reuters, product leaders from Daimler.

2. Like minded executives seeking innovation and travelling together with a shared organizing group — the Loire Valley Chamber of Commerce, Pasona HR consultancy, McKinsey’s banking clients.

3. Graduate-level education groups who were mid career and working for large companies — MBAs from London Business School, Cass Business School Exec MBAs.

We built a scorecard to estimate and track the effectiveness of our efforts. The scorecard also acted like a decision journal for our past judgements. We declined as many innovation tours as we accepted, even as we grew the program and our reputation with the tour organizers.

In 2019, we delivered over 50 innovation tours at Slack offices around the world and connected to over 550 new executives. These were slower developing leads that led to closed deals over the course of months and years. The more of them we could do, the more chances we had to tell the Slack story, build the value of collaboration and be part of prospective customers’ future options.

We made our goal to infect them with a mind virus: people were their largest investment and how well those people worked together — how well they collaborated — was the biggest performance differentiator possible. Therefore, collaboration ought to be the highest priority they could work on and Slack was the clear leading option for collaboration. We meant all of that only in the most benevolent of ways.

On a Personal Note

The work I have done over the last 3 years with the Executive Programs team has been some of the most fulfilling work of my career. We are a small and mighty team that aspires to a very high level of craftsmanship in all we do. I’ve found that incredibly inspiring and the best kind of hard fun to get to work on.

My boss was Marnie Merriam and she was the best boss I’ve ever had at any company. We coached each other. We acknowledged what we knew, what we didn’t know, and trusted each other to do our respective best work. I have enjoyed our working relationship immensely and will miss it.

And the executive programs team — they were always a pleasure to work with and achieved a standard of craftsmanship that I marvelled at. Team: You held me to account. You supported me. You challenged me and helped me be better. You laughed with me and made me laugh. Thank you.

I also had the incredible privilege to work with folks across the organization who always brought a mix of smarts and strengths, opinion and humility to each bit of work we did. They were collaborative and hard working. It was all 4 of the Slack attributes at once.

To our leadership groups, our leadership group’s support teams, our sales leaders, our product folks, our expert discussion leaders from across the business, our business support teams: thank you. Your partnership was invaluable to my work and you were excellent to collaborate with. One last time: thank you. I have been so incredibly lucky.

Aiming Towards Something

So, what now, fella? It’s certainly not retirement. Best to aim towards something, not just leave. Maybe it’s career 2.0. It’s a portfolio of things I want to pursue. It’s being a beginner again. It’s finding the beginnings in a few things.

More specifically, it’s 4 things, so far:

• Advisory work — I’ve started working with startups to help them. I have 2 I’m working with today and I anticipate 4-5 is the right number, in the Seed or Series A stage, with 2-20 employees. I think.

• Writing — It’s kind of where I started and where I’m often happiest — working on words and puzzling through ways to tell stories. Years ago I wrote a novel and made no money and I’ve always thought of that as my first novel. It’s not, yet, because I’ve not written another one. So I’d better get on that.

• Personal projects — Being a beginner. I have a crazy idea for a sculpture called Polytropos that retells the translations of the Odyssey. I have many other ideas. I will suck at the start, then get better. I’m playing drums.

• Volunteering and good work — To start, with the First Nations Technology Council. Then, water testing for Pacific Salmon Foundation. Mosiac to help new immigrants. Coaching kids sports.

Slack has been the best place that I’ve ever worked, by far. I feel like I was made for the work I did at Slack. I had trained all my life to be able to do it and it trained me to be better.

When I moved back to Vancouver from Dublin one of the things that I kept hearing in my mind is that work is love made tangible. Work is love made tangible. I always wanted to show people how much they meant to me in our work together.

In that spirit, this work has been the most rewarding and generous and hard fun I’ve ever had. I’ve loved working at Slack and with the Slack team.

And I believe the future for Slack is actually stronger than ever. I wish each of you the best of luck: tell the Slack story. I will be watching you do amazing things.

Thank you for every part you played in the last 7 years!

Up next — Questions That Remain: Thinking about luck. Money and MacGuffins. Leaving before it’s time.

And where to next next?

I still want your direction and feedback on where A Slack Story goes next.

Please take 1 minute and tell me what you’d like to see next from A Slack Story.

Thank you!

I’ve got some ideas. But I want to hear from you too.

Please take 1 minute and tell me what you’d like to see next from A Slack Story.

Okay, onwards to some stories I haven’t told you, yet.

Finding Our Frontiers

The software marketing playbook is very clear on this one. Once you reach a certain size, you start a conference. That conference brings together your customers, your partners, your product and your team — all your key groups of people.

The tone of the conference can be revealing and depends on the company. It could be an immense, sprawling and crawling fest like Salesforce’s Dreamforce. It could be niche and technically focused like Okta’s Oktane. It could be nerdy and striving to seem important like Twilio’s Signal. There’s some variance and latitude on how you direct the conference and how you signal your values.

But however you shake it out, you reach a time when you simply must create a conference. At Slack we knew it was time when customers started asking about a Slack conference. They wanted more Slack and they had a professional development budget to spend. So starting in 2017 we created Frontiers.

On the waterfront of San Francisco, in a cavernous shell of a cruise ship terminal, we set up a full conference experience: Slack product demonstrations, Slack customer stories, Slack tech talks — Slackity, Slack, Slack, day after day. It sold out in a few weeks and we did it again in 2018 and 2019.

For those of us focused on customers, Slack Frontiers created a compelling event to drive urgency on pretty much any timeline. We had found a persistent reality of corporate life — so much can happen because there’s a deadline and not much often happens without a deadline.

So if we could create a deadline, then we could make things happen. And so we did. Frontiers became a deadline. Is that ironic for a product called Slack?

By 2019, my last Frontiers conference, we had a full executive briefing program in place on site. We ran dozens and dozens of briefings each day, whisking folks into temporary rooms built for purpose, creating a cyclical ceremony of improvisation, juggling, chasing, calming words and then lining up to do it again.

Overall, Frontiers proved eclectic, delightful and a bit weird. Stewart interviewed Serena Williams on stage. A marching band closed a day of programming. Falcons and owls patrolled the oceanfront exteriors of the venues to scare away the seagulls. I have so many vignettes of those intensive days — conversations in snapshot, moments that anchor the experience. Meeting with Goldman Sachs tech leadership team and realizing the pitching was bi-directional: they were selling to us as we approached going public as much as we were selling to them.

The end of each Frontiers left our teams with a hangover of exhaustion and the glow of a job well done. We had gathered a few thousand customers, partners, media and other Slack-interested folks in one place for a few days and tried to maximize the progress we could make for the business with each of them. Every moment felt jammed full of ambitions and each evening we felt the elation of wringing the best from the day.

So one question you might be wondering — why call it Frontiers?

Stewart presented a Carl Sagan quote at the very first conference that acted as an orientation point to start our journey:

“We’re the kind of species that needs a frontier, for fundamental biological reasons. Every time humanity stretches itself and turns a new corner, it receives a jolt of productive vitality that can carry it for centuries.

— Carl Sagan, Pale Blue Dot

We wanted to think big and shoot for the moon. I’m sure it also helped to think of the aspirational elements of frontiers as an overt nod to US mythology, a western frontier and manifest destiny and man on the moon and so on.

The Sagan quote continues for two more sentences in that paragraph that Stewart didn’t include on his slide: “There is a new world next door. And we know how to get there.”

I can see why he omitted those lines because I’m not sure we totally knew how to get there. But I do feel good saying that we tried hard to find how to get there, along with our customers.

Almost Getting PIP’d

PIP: short for Performance Improvement Plan. Given to low performing employees to get them sorted out and on track (or back on track). Could also be the first step in managing them out, a euphemism for firing them with a track record of evidence to back up your decision.

I know about PIPs because I had delivered them to employees not meeting expectations. Sometimes they were hard conversations. Most often they were really good conversations that made explicit and overt an ongoing concern, and formalized a nagging worry into a codified process.

I also know about PIPs because Marnie brought the topic up in one of our 1:1s in January, 2020. She brought it up as a warning to me, meaning, I was on track to be on a PIP if I didn’t improve my performance. Who, me?

That came as a surprise. But really, should it have been?

I’d been coasting along pretty loosely. Logging in and keeping up but not really pushing much ahead in any way that needed to happen. It felt hard to keep motivated and focused on pushing myself.

We’d gone public in June, 2019. We’d kept running our programs — Executive Briefings and Innovation Tours and so on — through the balance of 2019. I felt pretty comfortable and pretty complacent. Not much felt urgent at all. But that wasn’t what my role needed. It needed some restlessness for new initiatives coupled with execution on the existing ones. I was just doing the second of those things.

So I had to reset after that PIP conversation. Did I want to be on a PIP? Nope, not at all. Did I want to be complacent or comfortable? Sometimes, maybe, but not overall.

It was time to give myself the hard word. Time to refocus. Time to say, hey buddy, figure out what you really want to do with your time and your contributions here. Don’t let it snuff out. Decide on how you want your story to go.

Accepting Less Ambition

At certain stages in my Slack journey I was challenged to accept less. To take on a smaller role, rather than a bigger role. To have a new person join the company and take over something I had done or aspired to do, or something I thought I could be good at doing. To be given a new boss without any say in the matter and to accept it.

Perhaps you’ve noticed this reading A Slack Story?

I won’t pretend that this was always easy. It was not. Each time, it was hard to give away my Legos.

I felt attached to things and invested in my work. I had ambitions and wanted to lead and play a leading role. I thought I had shown I was pretty good at some things. The internal and external feedback often seemed positive. I thought we got good results from the work I did and, turns out, hey hey, proof outside of what I thought showed we did consistently get good results. For each role I had at Slack I can trot out stats and stories of success. If you want that sanitized and rosy perspective, check my LinkedIn page.

But from a distance of time and perspective I could also look at my Slack journey as one of consistently getting demoted to smaller roles with less responsibility. That’s another important perspective that sticks with me and I think reflects what it’s like to be part of the journey of a fast-growing tech startup.

I started as the only Marketing person and so the Marketing leader. Then others came in and picked up that function and did it much better. The same with Sales. The same with European leadership.

Over and over again Slack hired better people than me to do the job I had been doing. Sometimes I even found and hired the people myself!

The people we hired were consistently world class. In fact, by pattern, they ended up being so strong so often that I could safely assume they were one of the top 5 people in the world fit for doing that specific job — because they were!

I consistently had amazing colleagues and was delighted by the quality of folks who I got to work with. It’s no bullshit to say they made me better and they certainly made Slack better than I could have, had I stayed on in the roles I left.

The phrase, swallow your pride isn’t really adequate to describe how it felt to become a smaller piece of a larger organization. Swallowing your pride seems like a phrase for a moment. It seems like a phrase about not saying something you feel an impetuous desire to say as a reaction to an attack on your status. To swallow those words of pride instead of spitting them out.

I find a more accurate way of thinking about my overall trajectory at Slack might be as someone finding new prospective parts of the organization to try to figure out. To be a kind of generalist pioneer, blundering ahead, with a tolerance for risk, heading out and doing something new that the organization needs done, perhaps poorly to start, before someone else can come in and do it better. An amateur with a bit of a nose for getting things done.

And I won’t lie, there was prestige too in having been the first to do things at Slack. I was flattered when new people joined and were impressed by something I’d done. By happenstance, I did receive many small votes of status because I had been there as the first person doing the thing.

Having this pioneering history was good but also dangerous. I found I had to have a 2-part relationship with it. In part one, I needed to hold it close and be reminded of it because it provided good guidance on how to operate. In part two, I need to let it go and stay humble because it didn’t necessarily help in the present.

Nothing stayed the same. I had been lucky and had worked hard and made mistakes and contributed valuable steps to the overall journey. But always I felt the nag of the question: what had I done lately? And when I didn’t feel the nag of that question, I knew it was time to reassess what I was doing.

When we had our first customer to charge over $1,000 I created an invoice in Word with our logo, exported it as a PDF and sent it to them. I don’t think we even had an accounting system to book the revenue in. We may have had tax numbers I may have forgotten to include.

When we had to hire people I created an evaluation matrix and interview questions based on what I thought made for good hires. When we had to sell to US government organizations I created a Fed.gov account so we could be listed as an official vendor.

Nothing really qualified me for doing any of those jobs. Except no one else was going to do them. So step right up, friend, and get it done.

Never Underestimate Sheer Gall

I once had a professor in university who I consider a mentor. I was an English student and he focused on writing poetry and short stories, proper post-modern literature.

A group of us students had started a publishing company to share our work with the world. At first, we asked him if we should do this. His answer I still remember today: “Never underestimate sheer gall.”

Many of the stories in this larger story I’ve been telling are available because I was there and involved and had a bit of gall. Yet all these things got replaced with better versions. And though I often felt more than a bit precious about the work I’d put in and the ways we did things, I had to ultimately let it all go.

What got us here won’t get us there was a frequent phrase I’d tell myself when going through changes. We had to burn the metaphorical boats. The way we had done things needed to change to get us to the next place we wanted to go.

As a generalist I had to get used to better experts coming in, and me needing to find a new place to belong. I had some measures of a happy-go-lucky attitude, an analytic perspective outside myself and an ability for creative, flexible problem solving. I could tell a story with data and anecdotes. I could tell a story with people and emotions. I felt like I could call bullshit on myself and others, in a responsible and respectful way. I could come up with an idea and I could buy into an idea someone else originated.

Those were the strengths that I consistently leaned on and that served me well at Slack. So if you’re reading this for career perspective, that’s about all I have to offer. Be you and be the best you that you can be.

I coach kids hockey now and I tell them that the bravest thing they can do is find out how good they can be. And I mean it. The bravest thing they can do is challenge themselves, cut out any excuses and really push to excel as well as they can. Sell out. Find out what it means to go after something with all their heart. Decide to do their absolute best and know that no matter what the outcome, their effort and desire and gall will matter. And I hope they hear me saying that it’s not just about hockey.

I once read that you can only write at the speed of your own self awareness. I think you can also only really understand your career (and your life overall) at the speed of your own self awareness.

So part of writing this story has been to find my own self awareness, and part of it has been to share it with people I care about, and part of it has been to share it with people I’ve never met and who could benefit from it.

And I hope it helps you all.

Up next — Thank you, Slack: Leaving after 7 years. What I’m leaving behind. Aiming towards something.

Did you already tell me what you’d like to see next from A Slack Story?

Then I appreciate that minute of your time. Thank you!

I remember the day very clearly because I wasn’t there. I was on vacation with my family.

On the morning WORK started trading, I woke early in a cabin in a town called West Yellowstone, just outside the boundary to Yellowstone National Park. Wifi reception proved spotty. We were a long way from the NYSE but still very much connected.

Going Public from Yellowstone

My wife had wanted to attend a conference in West Yellowstone for her work, and my son and I had decided to tag along. She had made a goodly number of sacrifices for my work at Slack. Here was a chance to balance the ledger. Plus, Yellowstone seemed a remarkable once-in-a-lifetime kind of place to visit.

So we made the decision to go. That was before the announcement of Slack’s public listing date. Then we waffled on our decision for a few minutes. Should we go? Should we not? We couldn’t be in two places at once. We decided to stick to our plan for a work / family vacation.

And I can’t say I didn’t have some FOMO as teammates posted photos from NYSE. But Yellowstone was its own unique and amazing place too.

And getting there proved half the adventure. We drove down from our home in Vancouver to Seattle for one night. We took the underground Seattle tour, a key feature of a Scooby Doo episode my son loved, A Frightened Hound Meets Demons Underground.

We flew from Seattle to Bozeman, Montana, rented a car and headed out into the wide valleys full of cattle and scrubby brush and black-barked trees. We drove on into the tight mountain passes full of conifers.

At the same time, many of my long-time teammates would have been sitting on flights to New York to be on the floor of the NYSE for the debut of Slack. I had some small second thoughts about changing our plans, but those second thoughts quickly dissipated.

For many years my career with Slack had been supported by our family, through late nights and international relocation and business travel. Now it felt like time to rebalance that equation.

WORK Starts Trading on NYSE

June 19, 2019: the night before Slack started trading. I logged in to our brokerage account and set up my orders for the next day. I could have just as easily being buying a pair of shoes or booking a flight. The website experience felt so pedestrian. All the mechanisms acted the exact same. Type numbers into a form. Click button.

But the meaning definitely felt different. With my orders for the next day I was making decisions for our family’s financial future that would affect the rest of our lives. No big deal, just typing a few numbers, clicking a few buttons, placing a few orders, deciding on wagers that could bring years of work to fruition.

Zoom out with me now from those numbers on that screen for some context that might be helpful.

Slack started trading on the NYSE in what’s called a Direct Public Offering (DPO). People often called it an Initial Public Offering (IPO), but that process was different. A DPO was simpler and faster because there was no underwriting investment bank essentially lining up orders and guaranteeing the debut price. We were taking a chance.

For me specifically, because I was considered an insider, the DPO route to market offered more flexibility for all insiders selling shares. The calendar flipped over and we could buy and sell immediately, just like anyone with a brokerage account. So on June 20, 2019, my vested WORK shares were available to sell, and I could buy new ones. In contrast, an IPO included a lock-up period where insiders (like me) could not sell or buy shares for 3-6 months after the public offering.

The downside of a DPO was it offered more uncertainty on pricing of each share right up until the day before trading. And since the pricing influenced how many shares we wanted to sell, we had one huge known unknown factor in our decision. What do you sell if you don’t know the price? So up until the day before trading we didn’t really know how many shares we wanted to sell.

Slack was able to do a DPO because of the strength of its brand and business. We used it as a signal of strength. We believed the demand for WORK shares was strong enough that we didn’t need banks underwriting the launch of the shares’ trading. To some, I remember it seemed an additional risk at the time to do a DPO versus an IPO. It was different and unfamiliar. But it also fit Slack.

Okay, zoom back in with me now. Did I mention our Yellowstone cabin’s spotty Internet?

The day of the launch of WORK I remember very clearly. That day, June 20, I woke at 5 am mountain time, 7 am eastern time. I checked the orders I had placed to sell some of my shares the night before. A mild wave of panic flooded my brain. None of the orders I had set up had been saved. Time ticked down to the opening bell. I scrambled to redo my orders. The wifi held up. I got the orders reset with 3 minutes to spare and then waited. I double checked the orders. I refreshed the page and they held on screen, entries in some database in some data centre somewhere in the world. I made the coffee, checking back over my shoulder to see if anything changed on the screen.

As the coffee brewed I logged on to the internal live stream being broadcast from our New York offices. The two stars of the show were clearly our CEO, Stewart Butterflied, and our CFO, Allen Shim. They held the floor and told a story about the mechanics of how the shares actually got priced for their debut of trading.

The day before, they had met with bankers in the bankers’ offices. The way they described it was somewhat like a scene from a Wall Street movie — The Big Short or The Wolf of Wall Street or Wall Street itself. People, in suits, intensely talking with each other in coded language and then at the same time intensely talking with other people by phone in the coded language. They were taking in orders for WORK shares to set the price they would debut at. Someone on this phone line agreed with the price. Someone on another phone line wanted a bigger allocation at a higher price. This was how the sausage got made. They were making the market for WORK before WORK hit the public market.

Stewart and Allen were part of the process but they were just passengers. The bankers did the talking. The bankers did the haggling. Stewart and Allen listened and perhaps reacted, or perhaps tried not to react too much. The pricing conversations went well. In the retelling I remember Allen saying almost sheepishly that they had gone very well. He couldn’t share the exact numbers but it was going to be a very good opening.

The Unreality of it All

As my coffee brewed and the market open approached on that morning of June 20, I felt two things at once:

1. Amazement we had come so far and incredulity at the thing we were on the cusp of accomplishing and

2. Disbelief that it could all actually happen there in that moment in a cabin in Montana.

Our financial lives could be changing in a single direction and in such a drastic amount, then we needed to tidy up breakfast and pack our snacks for the day. Make sure we had warm clothes because the forecast called for snow. It felt at once both unreal and very real.

The market opened. Web pages got refreshed and notification emails arrived in my inbox. Our orders got filled. Numbers started appearing that showed WORK shares had priced at $37.50 to start and then risen. It was all good news. I stayed logged on to the live stream as long as I could to share the moment, before I had to get myself going for the day and being a dad to a travelling 6-year-old.

Perhaps we went for dinner that night. Perhaps we had a special meal at the cabin that we cooked. I can’t rightly remember.

As soon as we left the cabin that morning, we had no Internet no cell signal and were insulated from the news for the balance of the day. We left the world behind in the cabin and went exploring.

My wife attended her conference. My son and I rented bikes. We rode through a forest on long single-track paths to the Madison River and watched fly fishers wade the riffles seeking trout. They cast their lines in great stretching arcs over the water, back and forth, seeking the right balance of distance and tension. We startled a mule deer buck with velveted antlers so large they could have been from a young elk.

We had our snacks on the river shore and chatted wth a retired RVing couple from South Dakota who had been on the road for 2 months. They told my son they needed to find a place to empty their “poop tank.” He didn’t know what to make of that, being unfamiliar with the needs of plumbing and septic systems and RVs, but asked me about it again that night. He was concerned about them: had they found a place to empty out or were they still carrying around all their poop?

We got back to the cabin before dinner and I had a chance to catch up on the news of the day, the world far away. Headlines trumpeted the successful launch of WORK. Teammates posted selfies on the floor of the NYSE, or on the street outside where a giant purple banner full of emoji hung. Clips from TV interviews appeared in Slack and our executives stuck to their talking points about the business — the market proof for a new way of working, the demand this signalled, the greenfield opportunities still to come.

As moments go in a working life, going public with Slack proved pretty great.

Acknowledging the Change

Internally, Stewart had a great framing of the whole event of Slack going public. He thought of it best described as a rite of passage similar to a high school graduation. It was a milestone to be noted and celebrated. It was important and well understood externally by friends and family and press and easy for people to point to as a marker of success no matter how well they understood our business.

And we’d worked hard to get here. Great! Let’s acknowledge our achievement.

But if going public proved the highlight of Slack’s journey, we would have greatly underachieved. There was still so much to accomplish. This was just one step along the way to bigger things.

I liked that framing very much and in the months to come I would repeat it to our guests on Innovation Tours, to our prospects and customers in Executive Briefings. They frequently asked how going public had changed Slack. They didn’t distinguish between a DPO and an IPO. It was all just Going Public. It was all part of the larger story of Slack that folks knew.

And in those sessions what I heard them asking — if they used these words or not — was whether money had changed Slack. Had it? And how was I to answer that?

Because truthfully, yes, money had changed Slack. Money had changed Slack, and many other things that came with money and growth had changed Slack too.

New people working at Slack with new ideas and new ways of doing things more reflective or a larger public companies. New competitors (chiefly Microsoft Teams) working against Slack, with our customers, with the press, with employees. New customers further back on the adoption curve trying to understand what the fuss was all about with Slack and if it should matter to them at all.

Those changes weren’t like a light switch that got flipped when Slack became WORK and started trading publicly. A huge amount of work and thought preceded that transition to make it as smooth as possible. We had started operating as if we were a public company many quarters before we were a public company. We had used our stock as a currency to acquire companies. We had bonus plans based on hitting financial performance targets.

It all felt very grown up from where we had started. And it all felt to me like a part of a continuum of growth: get bigger, get more conventional, get more conservative because there’s more to lose. All the important stakeholders in Slack (employees, customers, shareholders, etc.) got more conservative, so the company got more conservative in its decisions.

It still felt like Slack was somewhat the same place as ever. It felt like we mostly still embraced the same spirit of playfulness. It felt like we mostly still worked for each other and for our customers and that both parties benefitted — we got their business and they got a better way or working together. It felt like we mostly still could invest deeply in hard work to get the details right in the various parts of our organization, and that we celebrated that respect for getting the details right. It felt like mostly still being in the software business could still affect people and delight them and help them in small and large ways.

But consistently saying that what got you here won’t get you there means you have to change to something, and that something tends to be pretty conventional.

Change had to happen if we wanted to continue to grow. Was it all positive? No. Was it still overwhelmingly positive from my point of view? Yes, certainly.

I still really liked the people I worked with. I really liked the work we got to do together. I trusted working with them and wanted to keep going.

How much longer? That’s a good question, and one I had for myself too.

Up next: Stories I Haven’t Told You (Yet) — Finding our Frontiers. Almost getting PIP’d. Accepting less ambition.

Maybe!

Truthfully, I’d had a Slack pocket square on my mind for a few months before I started to do anything about it.

One first caught my eye in a shop in Heathrow Airport. I unfolded it from a display table and looked closer. It wasn’t quite right — the colours echoed Slack’s colours and fell in the right cross-hatched pattern, but the shades were off. It wasn’t the right number of colours. The fabric texture was too coarse. As a model of what I’d been noodling on, it worked. But only as a model.

I bought that pocket square and tried it in my suit jacket the next chance I had. People noticed: Oh cool. Is that a Slack pocket square? It was not, but it was close and its exactness wasn’t the point. The point was the noticing and the association and the question of whether it was a Slack pocket square.

Pocket squares had some style. We aspired to have some style too. This could work.

Finding New Partners

I did a bit of research and got in touch with a few suppliers. I met Jaspal from Monsoon Corporate Gifts in Montreal. They had lovely scarves, ties, pashminas, bow ties and (yes!) pocket squares on their website to demonstrate their capabilities.

Through email, Jaspal and I worked on our order — materials, dimensions, quantity, production considerations. The design felt solved with our existing cross-hatched tartanish pattern. Yet we still needed to find a border colour, a blend for the silk and a finish to the material (how matte or glossy it would show).

We got to an agreement on the details. On January 23, 2018, I called Jaspal and read him my credit card number. A few weeks later a box arrived to our Vancouver office filled with 250 Slack pocket squares. At least, that’s what I thought they were.

I showed some teammates. They had some different ideas as they unfolded the silk.

Oh, a scarf! A headband! A hairband! A handkerchief for my dog!

The immediate feedback was all definitely positive and it was also definitely in many different directions. Giving folks a 14” x 14” piece of silk with the now retired corporate colours invited many interpretations. Did I mention that the corporate colours were now retired? Yes, right.

And, confession time: the whole pocket squares project was off the books and unsanctioned. Grey market because I wanted to give it a try.

Slack’s marketing had matured and moved on, and rightfully so. We had hundreds of millions in annual recurring revenues, close to 2,000 employees and customers in 120+ countries. Experts were in charge and doing a great job and I was not one of them.

But I still felt like I could get away with a niche project like the pocket squares and run a covert mini marketing operation in Executive Programs. But it would only ever be small and niche and under the radar. Unless it wasn’t.

I started giving away some of my stock of 250 pocket squares, one by one, to folks who asked about them. I’d leave one on a teammate’s desk. I carried a stash of them with me when I visited different Slack offices. I handed them to co-presenters. I started getting some requests for them, or some requests for restocks from folks I’d already shared one with and who had passed theirs on. Unbelievably, dogs managed to lose their handkerchiefs. Woof!

And playing the role of the Slack Man, I of course wore my own pocket square. That prompted questions. People often wanted to know how they could get one.

My favourite thing to do when prompted for a pocket square was to pull my own from my jacket (unfolded with a flourish) and give it to them. This required me to have a few backups at all times, but was well worth it for the reaction it provided. The flourish made the sale and left an impression, a nod towards a magician’s conjuring.

Fooling Myself Into Options

The pocket square felt like a very small prop in the small performances I engaged in. Sales presentations, Executive Briefings, Innovation Tours, lunch and learns — all the ways we went about hosting and coordinating small groups of important people and helping them have effective discussions towards specific objectives.

Speaking felt like stage work, and, truthfully, it was. People made decisions of perception all the time with very little information. They sought out the signals they could find. They wanted to be introduced to Slack because our PR game continued to be strong. They’d heard of Slack. They wanted to learn and have a frame of reference to fit Slack into in their minds. They especially didn’t want to miss out on something cool like Slack.

In addition to pocket squares we had other executive programs swag made. Fancy umbrellas that went up and down from a spring-loaded handle, whose segments unfolded in an elliptical shape that made it easy to pass someone else holding an umbrella on the sidewalk, and slipped through the air so gusts of wind couldn’t flip it inside out. These were amazing and cost $30 each, way too much for a giveaway except in limited quantities.

For swag, we tried to keep a playful and professional and useful approach to everything we did. We tried to play to our strengths and avoid just having more random plastic crap people didn’t want. We wanted even our giveaway items to reflect our company values — craftsmanship, courtesy, playfulness.

In shooting for high standards in all the parts of our work I’d also like to think we made Slack a better place to work for everyone. No one wanted to aspire to mediocrity, yet it seemed so many companies’ swag outputs reflected mediocrity. Aiming high meant that even if we fell short we still ended up striking a good spot.

I don’t want to give you the impression we were perfect. We weren’t. We failed at things. We compromised. Reality consistently tamped down our aspirations, and sometimes we fell back to earth with some scorch marks. If socks were a 500,000 hit, pocket squares were more like 500.

But trying to hit high standards meant we chose our own challenges and then had to marshall our own gumption to reach them. We investigated space pens that could write in zero gravity and decided that nah, $100 for a giveaway item was too much. That kind of autonomy felt like rocket fuel to me and the folks I worked with, even if it was just in our own very small EBC corner of the organization.

It made the idea of leaving Slack nearly unfathomable too. We had momentum and money and amazing people to work with on hard problems. Why would anyone want to go elsewhere? We had our problems and we loved them, in the way that work can be love made tangible. We didn’t want to trade them for any other problems. Each day was mortal combat against our own limitations.

Did this Slack Man start to feel a bit like a Slack mascot with branded socks and laptop sleeve and pocket square? With my purple jacket and changing my accent so I pronounced process as prah-sess instead of pro-sess? Yes, maybe a bit.

But overall, that feeling felt pretty small. The larger feeling I carried was how lucky I was to have such a sense of play in my work with teammates, to be able to explore rich territories, to be able to fail or succeed, and to be able to try again with a flourish.

Up next: WORK on NYSE — Going public from Yellowstone. Finding the unreality of it all. Acknowledging the change.

Let me unpack that a bit.

To start, demand for Innovation Tours came to us. The world reflected back to us what we had been telling it: Slack was an innovator. Huzzah. Our PR was doing a brisk business.

People wrote to ask if they could they bring their Innovation Tour to visit Slack’s offices. To see the sights. Wander the halls. Take the innovation air. Along with other companies of the moment — Dropbox and Google and Uber — folks wanted Slack to be a stop on their Innovation Tour.

Really? This was our first reaction. We didn’t know how to respond. What was an Innovation Tour? Who were these folks? Why might they want to visit Slack? Why might we want them to visit? How did it all work? We tried to learn more.

We learned Innovation Tours came in many flavours. Sometimes the Innovation Tour was being run by a company (Daimler or AstraZeneca or Bosch) and the tourists were its employees. Sometimes it was run by a government agency (The German-American Chamber of Commerce, La Loire’s regional economic agency) and the tourists were its constituents. Sometimes it was run by a consulting company (Accenture, ThoughtWorks, Bain, BCG) and the tourists were its clients.

Most often, the Innovation Tour was run by a company that specialized in Innovation Tours. The whole company focused on it. They might also have added expertise in programming and education and corporate events to go along with the innovation tourism, but it was the Innovation Tours they specialized in.

We met companies like Austral Education Group, WDHB, Flyn, 10x, SVIC and many more innovation tourism companies. Often they called the Innovation Tours Journeys or Missions. They worked with large companies to create themes for the tours, driven by the specific innovation issues of the client, then filled the itinerary with experiences to address the theme (company visits, workshops, guest speakers, etc.). They tapped into budgets for executive education. They knew their business and I grew to respect their expertise and niche.

Now you might be thinking, how big can this really be? Is this a whole boutique industry? And I assure you, it is. If you run an irrigation company in Winnipeg with 30 seasonal employees like my friend Jeff, an innovation tour might sound mostly like a boondoggle. And it could be. A few folks on the tours treated them as such and showed up hungover.

But if you worked leading an innovation team at DENSO in Aichi, Japan — established in 1949, creator of the QR code in 1994 — and you wanted to see first-hand how business could work differently, an Innovation Tour could be a valuable and educational trip to see how Silicon Valley worked. Or if you led the software and systems teams at Airbus in Blagnac, outside Toulouse, France, an Innovation Tour could also act as a reward and team building event for a tiny subset of your 147,893 employees who have met a goal.

In short, we learned that an Innovation Tour could morph to serve many needs, connecting the tourists’ perception of their old thinking to the challenge of Silicon Valley’s new ways of thinking.

And as our profile grew, the volume of inbound inquiries for innovation tours to visit Slack kept increasing. So how could that become an opportunity for us?

We felt pulled in opposite directions. Saying No Nicely was something we had practiced to good effect in many domains for many years. We liked to stay simple and stick to our knitting.

But acknowledging that What Got Us Here Won’t Get Us There also meant we had to keep changing. So we decided to say yes and do some Innovation Tours.

Return of the Matrix

Like so many things we did at Slack, at first we tried to listen to the world and learn what it was telling us. Then we tried to find the easiest path to finding out if our ideas about what we thought we heard were real. We started small and validated our assumptions. We sought evidence outside our own wishful thinking.

And I confess, before we had any kind of corporate program for Innovation Tours, I had dabbled a bit. I got forwarded some inbound inquiries and said yes to a few. A team of ~20 innovation leaders visited our Dublin offices as part of an Accenture group. They wanted to learn about Slack’s culture, so I did an office tour and presentation for them that highlighted elements of Slack’s culture.

But could Innovation Tours actual be valuable for Slack’s business? I felt suspicious and like I needed some defensibility and rigour in my process if I was going to consistently say yes to doing them. So I started to track the people and organizations who visited and then reviewed how they affected sales. This tracking was the digital equivalent of digging a ditch with a shovel — inelegant but workable — and it helped see the results from Innovation Tours after they happened.

But that was a long lag to decide what ones should we host. So I revisited an old favourite decision making tool — the 5-factor matrix. Just like when we started hiring people, we had many factors we needed to weigh in decisions that we hoped were the right factors.

When I hired the first 5 sales people at Slack I had evaluated candidates on 5 factors — communication, integrity, poise, savvy, grit. What would the equivalent 5 factors be to evaluate Innovation Tour groups? Here’s where I landed:

1. Organization size — How big were the employer(s) of the visitors? Bigger equaled better because Slack billed by users.

2. Opportunity size — Did we have a deal in process with visitors? Did we have a past deal with visitors? Again, bigger was better here but we also kept an eye on new industries and upside over time to be found.

3. Slack usage — Did they have any? How much? More usage equaled better prospects. We also wanted to say yes to existing Slack customers.

4. Slack propensity — Did the people of the group seem likely to use Slack? Did they come from a strong Slack industry / company / region? White-collar, tech-focused organizations in WEIRD countries were best.

5. Participants seniority — Did the participants make decisions at their organization? Did they make technology decisions? The more decision makers we could connect with, the better for our business.

Just as with Sales roles, I scored each of the 5 factors out of 5 points (higher = better) and added up the scores. Scores of <15 were automatic Nos. Score of 16-20 were Maybes that needed a reason to get approved. Scores of >21 were automatically a Yes as long as we could make the logistics work.

I called the spreadsheet an Innovation Tour Scorecard, with capital letters to make it sound official. An added bonus I had not anticipated from the Scorecard is that it also served as a decision journal for our past judgements so we could see if the factors we considered mattered and if our decisions made sense. Spoiler: they did and they did.

We added every invitation we received to the spreadsheet so we could also see the ones that scored too low and that we declined, and we declined about twice as many Innovation Tours as we accepted.

Okay, so we had a process in place and some accountability. All we needed now was a memorable, meaningful story to tell guests on our Innovation Tours.

Harnessing Our Story

Right from the start we had lots of advantages to make Innovation Tours work. The PR work our team had done set the stage with our public story. People arrived with some awareness and a positive sense of Slack. Our offices were lovely courtesy of our global facilities teams.

And our story was rooted in innovation, right from the start when our CEO had laid down a great quote to build on:

The best — maybe the only? — real, direct measure of “innovation” is change in human behaviour. In fact, it is useful to take this way of thinking as definitional: innovation is the sum of change across the whole system, not a thing which causes a change in how people behave. No small innovation ever caused a large shift in how people spend their time and no large one has ever failed to do so.

— Stewart Butterfield, We Don’t Sell Saddles Here

So how to put all these ingredients together and make something remarkable?

To start, the groups expected a tour on their Innovation Tour. So tour them about, I did.

I met our groups in the Slack HQ lobby in SF. We had a 10-storey building full of Slack people and work and all the physical infrastructure and cultural manifestations that made that possible. People wanted to see it all. But no, that would have been impossible. So we focused on hitting some highlights and leaving them wanting more.

The first stop, once everyone was signed in, was Everest. Everest was a literal photo of Mount Everest in our lobby. It was huge. In memory, I’d guess 8’ tall by 12’ wide, shot from a satellite and incredibly high-resolution. It made you feel small. I gathered the group close to it for the full effect. I asked them to focus in on a detail. Minuscule among the rock and ice and snow we could see a few dashes of colour — yellows and reds. That was the Everest Base Camp. We still felt we had Everest to climb in our business. That metaphor was where we started.

The tour continued upwards. We visited the all hands and lunch space to show them how Slack came together over meals and meetings. We stopped at the library on 5 to show them quiet spaces for contemplative work. We passed artwork, poked our heads into meeting rooms. I had talking points on design and enabling everyone to do the best work of their lives. I mentioned the use of light and plants and oxygen, how meeting rooms mostly had been built on inside walls to keep outside windows available to everyone. Guests asked about our desks set up — did each one adjust seated to standing? Yes.

We eventually ascended to 10, where a coffee bar awaited, sun lit and ready to make cappuccinos and affogatos. I showed them into our Executive Briefing Centre (EBC), a lovely corner meeting room, windowed on two sides and prepared in all ways. I let folks put down their things, get settled in that room, and invited them to place their coffee orders with the baristas. Maybe I showed them the secret mezzanine lounge. One of the top questions was always directions to the bathrooms.

Through all this it felt like all of a sudden we were running a hospitality business. When we had started as 3 people in a Vancouver office we’d talked about Four Seasons’ customer experience as an inspiration, something we aspired to but delivered in a software experience.

Now we had to drop the metaphorical distance and apply that inspiration to actual place making and hosting for people IRL. I suppose the name Innovation Tours should have tipped us off.

Do you care about any of this? Maybe. Maybe not. Same as our guests. As we were immersed in it, we felt our approach needed to match up to the experience we expected from our software. A lot of complex and detailed work had to happen behind the scenes to make the experience of the guest simple, smooth and coherent. We had to strike a balance between security and hospitality, sharing details and overwhelming tired travellers.

If everything went well, maybe no one would even notice any of the sweat that went into the user experience. We’d skate by on the sprezzatura of it all.

5 Lessons from Building a Culture of Innovation

Now that we had our guests suitably introduced to Slack — arrived, toured, caffeinated and curious — what story did we want to tell them?

I created a presentation called Building a Culture of Innovation. Over the years I delivered it many hundreds of times, and it evolved as I gave it. Other folks delivered it too, often with their own spin and stories included. I’m not going to include the whole presentation here (Boring! Leave a comment if you want it.) but I do think I learned some valuable lessons doing the presentation so many times.

Here’s the top 5 lessons I still return to and share with folks:

1. No one remembers what you say. They remember how you made them feel. This has been said so many times and yet still bears repeating. That’s why we felt we were running a hospitality business. How do you want to make people feel?

2. Assume no one knows you. No matter how good your PR, assume folks don’t know your story and you’re going to have to start at the beginning. To make this concrete, I often would ask a group, hold up your hands, 1 finger is not at all, 5 fingers is really well, and tell me how well do you know Slack? There was always a range of answers. Great. Then I had the chance to say, let me start at the beginning and do an introduction (or reintroduction) so we’re all on the same page and can go forward together.

3. Contract the talk. You’re making a deal with the group — they’re going to pay attention and you’re going to reward that attention. But for what? I liked to do this on the agenda slide, right after I established the need for an intro because of the range of answers to how well folks knew Slack. I showed a 3-item agenda and asked — is there anything anyone wants included not covered by this agenda? Sometimes people asked for something specific and I’d make a note to cover it. Most times everyone was happy with the agenda. In either case, it gave the audience a say in the proceedings and then let us all move on together with an agreed-upon structure. Okay, let’s go.

4. Rule of 3s. It just always works. Three main presentation sections. Beginning, middle, end. Three subsections within those main sections. Job done. Unless absolutely essential to deviate, I always defaulted to using the Rule of 3s. It’s simple, clear and effective.

5. Include subject matter experts. I always loved to have someone else to present with me. It kept the content fresh and the guests engaged. It also made it simple to bounce ideas off each other and build on points with each other. I asked my experts to tell stories from their working life at Slack, to show how they used Slack. Folks loved to see behind the scenes and all the details of both good and bad stories, lessons and mistakes. If live experts aren’t an option, include videos.

I could go on for some time about the above lessons and more. I learned a lot leading the Innovation Tours at Slack. It’s a deep vein I thought about often and took pride in doing well. All those reps gave me a ton of practice too.

And I should also mention that in addition to the tailwinds that benefitted our overall business, I had a huge personal luxury. No one at Slack was paying attention to what I was doing. No one asked about my presentations. No one approved my presentations. No one told me the story to tell. I sewed together the Building a Culture of Innovation story from many threads: Carol Dweck’s Growth Mindset ideas, sales presentations, game theory, Calvin and Hobbes comics, Steve Jobs videos, change management books.

By 2019, my last year at Slack and the last year before the COVID pandemic closed down Innovation Tours, we had 3 Strategists doing Innovation Tours. We delivered over 50 Innovation Tours at Slack offices around the world and introduced Slack to 550 global executives. It felt kind of like found money — an unexpected $20 you discover in the pocket of your jacket. My janky tracking reported we closed 29 deals in 2019 that started with Innovation Tours.

So something was working. The Innovation Tours deals came from slower developing leads, in deals over the course of quarters and years, not weeks and months. But we had faith that the more we did, the more we’d close. The more chances we had to tell the Slack story, the more chances we had to build the value of collaboration inside an organization and be part of prospective customers’ future options.

Or, as we put it internally, to infect our visitors with a mind virus. Once exposed to it, they couldn’t be inoculated against it. The specific mind virus we wanted to infect them with? That collaboration — how well their people worked together — was the highest priority any organization could work on, and Slack was the clear leader for enabling collaboration.

So from nothing, we created something. From taking a chance and listening to the world, we built a new source of business. And from an unnoticed market space, we found our story of innovation.

Up next: Pocket Squares — Falling for swag after socks. Finding a new partner. Fooling myself with options.

Well, yes, sometimes. Maybe even often. No one says, gosh, I’d love another meeting on my jammed calendar. That would be perfect.

But let me ask you to take a deep breath here. Clear your mind, because I’m about to make the case that meetings — done right — can be a beautiful, fiercely efficient way to run a business. And meetings — done right — can be the most effective way to close deals and create breakthroughs to achieve objectives. Okay, clear?

I’d like to start with the basics. We’re humans. We’re at our core social animals. As much as we sometimes forget, we’re designed to connect, negotiate, coordinate and communicate face to face with other humans. We’re optimized for it. Our voices, gestures, facial features, memory structures and more all point to a species purposefully made to meet each other. It’s inherent in us.

So how do we do meetings right?

Meetings Bloody Meetings

I’d also like to remember that meetings aren’t new, and frustration with meetings isn’t new. Take a trip down memory lane with me.

From 1976, I encourage you to review this half hour (!) video by John Cleese called Meetings Bloody Meetings. Sure, it’s a corporate how-to video at its core. But I promise, it’s funny and entertaining. As a bonus, you will be funnier and more entertaining to your colleagues if you watch it.

(Intro: John Cleese, in bed with his wife, complaining about meetings. In his papers, his wife has found a court summons for speeding and reminded Cleese to be on time for a family commitment on the same day.)

“No, no, it won’t take long. It’s a court case, not a meeting.”

“Well, they’re all the same thing really, aren’t they?”

“What?”

“A lot of people in a room trying to establish what happened and why, then deciding what to do about it.”

“Nothing like each other at all. In a court you have rules, procedures, it’s all organized. In meetings, you just…meet.”

(His wife turns out the light as he yawns in the semi darkness. Transition to Cleese in a dream about being on trial for running terrible meetings. He learns 5 steps to better meetings. End.)

The 5 steps suggested in the video for having better meetings?

1. Plan — Decide on precise objectives. List the subjects to cover.

2. Inform — What is being discussed? Why? And what you want from the discussion? Anticipate what information and people might be needed. Make sure they’re there.

3. Prepare — Prep the logical sequence of items, time for each item, based on importance.

4. Structure and Control — Take evidence, then interpret, then action. Stop people from jumping ahead or going back over old ground.

5. Summarize and Record — Summarize decisions and record them with the name of the person responsible.

Hmm. That’s a decent list. Definitely better than no effort to run a meeting. Even some overlap with the process we used at Executive Programs at Slack.

Steps 1 to 3 we applied pretty much as stated, with some massaging for context. Step 4 though, we did not use. Having people jump ahead and jump back was often very valuable. If we cut off the exploration of a topic we cut off the chance to learn about it and include its lessons and context in our process. Step 5, we definitely used.

But wait. I’m jumping ahead now. Step 4 goes for writing too!

And We’ll Call Them Briefings

So how to resolve the tension between the fact that no one likes meetings but meetings are what we’re optimized to do? Our answer: reinvent meetings as Briefings.

No, no, it’s not a meeting. It’s a Briefing — an Executive Briefing. Reinvention happens all the time with good results. Convection oven? No. Air fryer. Mouth detergent? No. Toothpaste. Names are the hangers of meaning.

Working in Executive Briefings we had a mandate to create the best kinds of meetings, with strong preparation, execution and follow through. We didn’t invent the concepts. Many other companies also ran Executive Briefing programs. But we did pioneer the concepts at Slack and make them work for our team.

And to make it all work, we needed to collaborate with 3 key groups.

1. Slack Sales — Our teammates working in Slack Sales on large accounts, as well as their managers. They defaulted to be strongly supportive of doing briefings, because any time they could get with their customers’ executives seemed great, and getting time with the Slack executives seemed good too. No harm in looking good for the home team.

2. Slack Executives – VPs and C-level titled folks on Slack’s executive team who got sequestered in to help advance deals. They defaulted to mildly supportive of doing briefings, in principle, because they were all good team players. But they also remained cautious of any demands on their time. Did it have to be them? Did it have to take so much time? How could they succeed with their role in the briefing?

3. Customer Executives — VPs and C-level titled folks at Slack’s customers. They fell into 3 big groups with slightly different reasons for why they might care:

   1. Line-of-business leaders (VP of Engineering, CTO, VP of Customer Service): They ran a large team at a customer. They wanted to know how Slack was relevant to their part of an organization and how it could help with their specific organizational goals. They could sponsor a deal (give a Yes) and often ended up as some of our best contacts.

   2. Line-of-responsibility leaders (CISO, CTO, CIO, VP of IT): They ran a function at a customer. They wanted to know in depth how Slack worked and integrated with their organization and systems. They could block a deal (give a No) on security concerns or pricing concerns or technology vision concerns but rarely sponsored a deal.

   3. Organization-wide leaders (CEO, CIO, CTO, CHRO): They ran a team and a function at a customer. They wanted to know how Slack could work for their whole organization and what it could do for them. They could both block a deal and sponsor a deal.

That’s all pretty abstract so let’s dig into some examples.

Michael Lopp was Slack’s VP of Engineering as well as being a semi-famous writer on engineering culture under the pen name Rands in Repose. We had lots of engineering focused deals on the boil at Slack NYC. We brought in Lopp to do a series of briefings with customers’ Engineering leaders at our Executive Briefing Centre. Lopp showed them how the Slack Engineering team used Slack. How he used Slack. How they could use Slack. He talked about the culture fostered by using Slack at Slack.

Ilan Frank was Slack’s VP of Enterprise Grid (our product for large customers). Those large customers grew in importance and wanted much more access to Slack’s leaders. They wanted insight into the product roadmap — when was their pet feature coming? We wanted to sell them on our future vision of collaboration. To join and serve both those interests we created a briefing series called Slack Product Roadmap and Vision. We ran it dozens, maybe hundreds of time. It used our roadmap to lead into showing how our vision came to fruition.

And of course, there was Stewart, Slack’s CEO, main spokesperson in public and boss. Everyone in all 3 groups above wanted to meet with Stewart — he was a star. And Stewart’s time was one of the most closely guarded secrets of Slack. As such, if we got a glimpse of Stewart time, we’d often create a briefing or series of briefings. We also reserved Stewart’s time for only the largest or most valuable customers’ briefings.

Sometimes the content and discussion of briefings was feature / function focused on releases in the next 3 quarters. Sometimes the content and discussion was much higher level and more strategic — How could Slack enable an international acquisition? How could Slack improve employee retention? How could Slack activity visualize and provide insight into communication pathways in an organization and then correlate those pathways onto team performance? Sometimes it was a blend. It all depended on the objectives we sought to achieve with a customer.

No matter who we ended up working with or what we ended up discussing, our goal at Executive Programs team was to run our process. People got tired of hearing about our process, but it worked and ensured a scalable, predictable, repeatable experience that positioned all 3 of our key groups to succeed.

We always started out gathering lots of information, consolidating it into one place, reviewing it as a team, doing a pre-briefing, doing a walk through, running the briefing, then doing a de-briefing to improve, debate and decide on next steps. Rinse and repeat and improve and let’s go.

Slack Sales Hated our Process

I’ll just say it at the start and get it out of the way: the key people we had to work with — #1 of the 3 groups above, Slack Sales — consistently kind of hated our process. Maybe hated is too strong here? Chafted against it, defintely.

To them, I heard it felt cumbersome, painful, onerous. Filling out forms? Putting some thought into objectives? Specifying outcomes they sought to achieve? Specifying outcomes their customer sought to achieve? Oh man, no joy. Couldn’t they just set up the meeting themselves?

And sure, they probably could go around our process. We were an internal service provider without much of a stick. Our Legal team were internal service providers too but no one could go around them because that’s how deal terms got finalized. Our Revenue team were in the same boat — no one could go around them because that’s how pricing got concluded. We didn’t have a similar consolidated power. We had to use much softer tactics.

Mainly, I had to create relationships with our sales managers and Account Executives. I had to stay on top of deals as they got to the right stage for a briefing, and what executive(s) we could use to move those deals ahead. I needed to have success stories to tell our sales team about Executive Briefings we had done, to give them ideas and to connect our work to the effects on a deal. In short, I had to sell our internal team on using our internal services.

With some Sales teams this proved easy. They welcomed the help. They often came from places with strong executive briefing programs. Or they did a briefing with one customer and then wanted to do the same with all their customers. Hot damn.

With others, it was hard to sell our services. They felt a sense of ownership over their deals. They didn’t want to share. They didn’t want things happening on deals outside of their purview. They didn’t see why they needed to follow our process. Couldn’t they just DM Cal and get him to join a meeting with their customer’s CTO? Sure, give it a try and see how it goes.

The good news is I never felt threatened when folks didn’t want to use our services. We had no shortage of demand. Following our process meant the sales managers were happy, the assistants of Slack’s executives were happy. And the results started to roll in positively too.

Slack Sales Eventually Loved our Results

So though our process was a bit of pain for Slack Sales, the other 2 groups of folks we worked with all the time — Slack Executives and Customer Executives — loved working with our process. That was mostly because they had people to do all the painful parts. Then they got to experience the tight, objectives-driven agendas, the pre-briefed speakers, the nice touches like catering and swag.

For Slack Executives, if we ran our process well, they could be confident that when they showed up they would be set up to succeed in their role. They had gotten a written and in-person pre-briefing. They knew the talk track expected of them. They knew who they were meeting with from some background details on all attendees.

And right, the results. They were very good. Slack Sales, once they got through the process, loved the results. And of course, we tracked them as part of our process. Here are the headlines:

• Having an Executive Briefing meant a deal had a 77% win rate, versus a 33% general opportunity win rate.

• Each year our contribution to the business grew and in my last year that meant we touched deals worth $94-million in annual contract value.

There were big, standout wins and many steady, smaller wins. I’m happy to be able to say the team I worked on did good work daily and it paid off in the big picture. We did 500+ briefings in my last year with top customers like IBM, McKinsey, Apple, Oracle, Nike, Lockheed Martin and Verizon.

This all feels a bit braggy now, so I’ll wind it up. It was great work to have and I was lucky to do it. I was even luckier to work with a great team around me.

I think if my experience doing Executive Briefings taught me anything it’s that competitive advantages are often hiding in plain sight and look like hard work.

Taking an essential business process people generally overlook — meetings, in this case — and doing them as well as they can be done can be a competitive advantage. Being thoughtful and expecting execution at a high level over and over again can be a competitive advantage. Having the luxury to spend the time on the details and to get the process right can be a competitive advantage.

So meetings bloody meetings might be a popular sentiment and an easy label to avoid engagement or improvement in something we’re built to do. But in that frustration lies an opportunity and a reinvention of meetings to Briefings.

Up next: Innovation Tours — Harnessing our story. Finding a new decision matrix. Building a culture of innovation.

When I first found out about my new title, it sounded pretty soft and nebulous. A bit like a Brand Ambassador or an Influencer. Pretty bumpfy and frothy. The job title equivalent of too many pillows on the bed. A symptom of the times of zero interest rates and easy money for startups. Not essential like Engineering or Sales or HR or Marketing. A luxury and an indulgence. Probably the first to get cut in any downturn.

At the same time, since it all felt pretty undefined, the job presented itself as open for me to define what it meant — through intention, then action, then results. No one else at Slack was a Strategist or had ever been before me. Hardly anyone else knew what to do with my job (with the possible exception of my boss Marnie). So I realized I got to figure out what it meant to do the job and put my name on it. That sounded fortunate and familiar because it’s pretty much the same as I’d done with all 4 of my prior jobs at Slack.

No one had done Marketing before me at Slack. No one had done Sales. No one had been a Sales Manager. No one had opened a new office. So this new job linked up to the chain of my prior jobs as one I had to figure out as I did it.

And when I put it that way to myself, everything felt more substantial and promising. And I felt pretty keen to get started.

Making Up the Job

At the start, the job focused on executive briefings with some public speaking sprinkled in. I introduced the job and team and Marnie in meet the new, new, new, new boss. That hybrid job I had started lived in a specific time and place — in Dublin and Europe, before we relocated back to North America.

Then once we’d landed back in Vancouver, I got started on the intended job. It’s the job I did for the longest at Slack and it’s the last job I did at Slack. And, as I did the job, I found out what it could be. The job grew. By the end of the first year, the job had become like a portfolio of activities, all focused on moving ahead conversations about Slack.

Those conversations converged into 3 types of work:

1. Executive Briefing Centre (EBC) engagements — Working with our account teams to build agendas to advance conversations with our customers. This was about 50% of my job.

2. Investor and Partner engagements — Working with our investors like Andreessen Horowitz (a16z), Google Ventures and Softbank and our partners like ThoughtWorks, Bain and Accenture to introduce Slack to prospective new customers. This was about 20% of my job.

3. Innovation Tours — Working with professional education providers, embassies, chambers of commerce and government teams to host visits to Slack for their touring groups and introduce them to Slack’s culture. This was about 30% of my job.

I’ll spend a bit more time in the next few posts unpacking each of these 3 kinds of work because I think they each offer their own lessons about where Slack existed at the time in its development, how business worked behind the scenes and what software companies can do to grow.

For the rest of this post I’ll try to unpack the common elements of my job that persisted across all the work I did.

Being the Slack Man

That’s what people said to me as I performed my job, “you’re the Slack man.” I heard it enough times in all 3 parts of my job — working with our account teams and customers, pitching at a16z’s EBC on Sand Hill Road, hosting an innovation tour of 28 executives from Fujitsu — that I gave up my resistance of the label and embraced it. Okay, I could be the Slack man.

I never talked about being the Slack man with any of my peers. I hardly dared to even name it to myself. But that was the main role I had to play for our business.

And if I was going to be the Slack man, I needed a uniform. My friend Darren used to say, “clothes are costumes, costumes are symbols, symbols are powerful.” So I tried to take that cue from his theatre background and embrace it.

I had a purple jacket made. I also had some dress shirts made. When the tailor asked me if I wanted my personal initials on the cuff I declined, then asked, could I have anything on there? Anything that’s 3 letters, I learned. I had OMG embroidered to peak out and remind me to keep my sense of wonder. I wore my Slack socks.

Wearing a uniform made packing simple for all the travel I had to do as the Slack man, and I was into that kind of simplicity. I stayed at the same hotels if I could. They had good locations, reliable beds and decent gyms. I ate at the same restaurants. They had good locations, reliable service and healthy options. The Slack man had to take care of himself to keep going.

The thing I never anticipated about business travel is just how much time you end up spending on your own. You have to get good with your own company because you spend a lot of time alone. I started to collect and read the new editions of the 75 Maigret mysteries from Compass Books at SFO. I passed through with enough frequency I could order them and pick them up within a week or two.

One of the best parts of Slack man life on the road proved to be the chance to explore the destinations. In London, I had established a habit of walking from the office to my hotel each night. As I kept exploring cities, I found reservations for one at restaurants simple to get. Anywhere had a single seat for me and I had my book for company.

I know I’ve used this metaphor before, but it’s perfect here as well. The Slack man life felt like I was a stone skipping across the surface of water, of work, of Slack. I had a travelling identity as the Slack man. I had a home identity back in Vancouver. I kept on keeping on.

On the road I got to connect with specific customers with their account teams. I got to work with our executive team and set them up to succeed with customers. I got to represent Slack to the outside world in small gatherings. I trained myself to say ‘PRAH-sess’ as the Americans say it instead of ‘PROH-sess’ as Canadians do. The Slack man had to blend in and not offer any reasons for suspicion or foreignness.

Sometimes our goals were best served with me back of house, formatting the data of guest lists to get badges printed or updating a CRM or coaching account teams to narrow their agenda, to prompt an executive for a specific strong talk track, give them stories of other accounts they could learn from. Sometimes I was front of house facilitating a discussion, touring guests through Slack’s offices, introducing our executives and building on their answers to questions.

It was fun and frustrating at times. It was hard and easy at other times. I enjoyed pretty much every day of its contradictions.

Fumbling Towards Legitimacy

In the chapter on gentrifying Slack with Radio London I wrote:

In a world where no one knew anything and everyone was trying to thin slice their way to some sense of what was happening, who was important, what they should bet on, an office address and fit out could provide a powerful clue.

I think that’s right about its topic — an office address and fit out — and far beyond too. It’s right about all kinds of things in our world. It’s right about software certainly. What to buy. What to align with.

Way back when we got started, when we didn’t sell saddles and marketing was something we all worked on, I learned that we had the chance to create a new reality for our customers:

If anyone had asked me before my Slack journey whether beliefs drove behaviours or behaviours drove beliefs, I would have answered that it didn’t really matter in marketing. It could be either.

But for a new product, I wanted to work on changing people’s behaviours, not their beliefs. To change their behaviours was easier and faster. I didn’t have to convince you a Big Mac is good for you or a smart choice. I just had to tell you about it when you’re hungry, and to have a restaurant nearby that can serve it to you quickly, reliably and cheaply. You can buy something whether you believe in it or not. Then once behaviours are changed, the human intolerance for cognitive dissonance acts to change beliefs. Maybe that Big Mac isn’t so bad in a pinch. At least, that was what I believed before Slack.

What we were proposing to do was the opposite: to change people’s beliefs so that they changed their behaviours. It was very risky. We needed them to believe a better way of working was possible to try our product. They already communicated, so what if they could communicate better?

Now, as the Slack man, I had the chance to refresh our vision of how work worked and give people a story to believe in.

But me telling you this as a tight, coherent story masks how we got there. It wasn’t fast and it wasn’t clear. It was haphazard and eventually got headed in the right direction. I’m compressing that flailing to create simpler through line of why I could be the Slack man. I had been preparing for it since I started at Slack and just luckily stumbled into the role at the time the role got created and needed someone.

It meant I had already been to a series of a16z briefings at the Rosewood London, where I held the front door open for Kate Moss and she said, “Tah” and then I had descended to the basement ballroom to tell HSBC and Standard Chartered and Barclays and Lloyd’s about Slack. And I could draw on all those experiences to help myself and the folks I worked with make sense of the moments we shared.

“Legitimacy comes from selling the future,” says Steven Sinofsky as he provides a video and written crash course in how enterprise software has gotten sold over the past 50 years. And Sinoksly should know! He ran Windows as part of a 20+ year career at Microsoft, and he had to learn to sell the future (just as I had to learn to sell the future) as part of their executive briefing programs.

Microsoft had an Executive Briefing Center where we would host CIOs all day, and all the Microsoft product people would give talks to convince these buyers that you had a strategy and a master plan. I went to the first one of these meetings, and I remember thinking, “This is the dumbest thing I’ve ever been to.” Because I came in, ready to do a big demo to talk about the product - “Here’s Office 97, it’s great”, and all they wanted to hear about was my Ten Year Plan.

And, here’s the best part, you get rated for your presentation. And I got crappy ratings. Steve Ballmer, who was running the enterprise sales force, told me point blank, “This cannot happen!” This was a hard lesson to learn. Because, as the person who shipped the product, all you can think about is this mountain you just climbed to make that moment, and that demo, and that feature, possible. But all they want to hear about is, “What is Word Processing going to be in 10 years?”

So what was Slack’s vision of how people communicated in 10 years? That’s what we needed to figure out and that’s the question I (and many more amazing people) would spend the rest of my Slack career working on.

Up next — Briefing the Executives: Running the EBCs. Finding a vision / reality balance. Selling a future through the roadmap.

I remember opening the sliding door that first morning back, early after a short sleep, still on a transatlantic time zone, and feeling like we had made the right decision to come back. The air smelled sweet and dewy. The dawn light fell soft and purplish over the water as the sun rose.

Had we really considered moving to San Francisco or New York where Slack’s Executive Briefing Centres were located? For a few seconds, yes. We could have continued our international adventure and immersed ourselves in the thick of the struggle. We could have been at one of the centres of the action. But not really.

Our son returned to Vancouver as a 4-year-old with an Irish accent. He said, “budder” which he spread on his “tost” and put his crumbs into the “rubbish bin.” He had kindergarten entry coming up. Life decisions felt like they demanded we put down roots and Vancouver felt like the place we want to be, to be back to.

I have always found returning to a city can be a bit conflicting. Is it the same or not? Yes and no. What has changed? What has stayed the same? Will it still feel familiar and like home — even though you may have changed?

When people asked about Vancouver I frequently told them that it’s a city of 2.5-million people where there shouldn’t be a city. The mountains and ocean and rivers make it hard to build. They dwarf anything that does get built. Compared to some cities it’s small. Compared to other cities it’s large. Taken for itself it’s a mirage of a city at the edge of a continent. And now, living there again, it felt like our home.

Home Again, Home Again

After a few days getting settled, I rode my bike in to the Slack office to get back to work. The location of the office remained the same as the location I had left, yet everything was bigger.

Where we had occupied 1 floor, now we occupied 3 floors of dark desks and glassed-in meeting rooms. At some point we had punched through the third floor to join it to the fourth in a gathering area with bleacher seating. The 18” x 18” solid Douglas Fir beam that had been removed became a coffee table in a common area.

Each team in the office had grown and staked out areas on their respective floors. Design and engineering on the 4th. Sales and Customer Success on the 3rd. Customer Experience and Product Support on the 2nd. The kitchen pulled us all together for coffee, snacks and weekly lunches that occupied a large role in our collective imagination and office culture. We went hard on lunch.

A taco shop had opened on the main floor of the building. Our back stairwell provided us immediate access to their facilities so we could keep up our strength. A gym and a bike room lived in the basement with showers and a locker room. It never didn’t smell a bit musty but it also proved a terrific luxury for those of us who cycled in or wanted a quick workout.

And who filled that office? So many of my favourite people. Old teammates who had grown. New teammates who I got to know as consistently upholding the standard of how good our people could be. The place felt familiar and fresh at once.

And I mean that as no bullshit. The people at Slack continued to be amazing. Product support experts. Sales development representatives. Interactive designers. Javascript engineers. Each got a lot asked of them and each excelled in their job.

It’s the People, Again

Are you tired of hearing me talk about the people at Slack? I’ve certainly gone on about them. Way back in June, 2013 it had been the first reason I joined the company. It was my answer to Stewart when he asked back in Dublin what made Slack so special. It’s still what I remember years after leaving. And I’d still say it’s true — it was the people that made the place so special.

So I’ve likely banged on about it enough. But let’s dig in a bit more to some questions that led to the exceptional people.

For example, when they got hired at Slack were the people of Slack already excellent at their respective jobs? Maybe. They certainly had some solid track records to get hired in the first place. They were probably pretty great.

But I think each of us who worked at Slack would also agree that something at Slack contributed to our excellence at Slack. Something about the overall challenge the company faced, the humane way we approached work and the luxury of resources (time, people and money) we had as tailwinds but mostly never took for granted. The way we communicated with each other. The formalized and informal ways we worked together. The common mission we seemed to share and each be happy to contribute to. For lack of a better word, the company mission.

Slack people were terrific and Slack made each of them better too. I’m a pretty firm believer that all the tailwinds we felt made each of us better at our jobs than we could have been in any another situation, at any another company. They certainly made me better that I would have been elsewhere.

Each of us worked in our own jobs and did them well. That’s pretty basic and expected. The bonus multiplier was that each of us also had a pretty rich inclination towards learning more about how we could do our jobs better. Then we each talked to each other. Ideas spread, got challenged, got cross pollinated with related ideas. You get it and it compounds. Lots of smart people working hard to get better together acted as both rocket fuel and catnip.

To provide a bit more context on how the environment drove the excellence, I can only recall one person ever not measuring up and needing to be fired. They made the mistake of joining Slack and ending up more inclined to being extractive than we were. Too much mercenary, not enough missionary.

Much more commonly people got poached to other offices and leadership roles within Slack. The company grew and these folks grew into new spots in the company.

Here’s a quick incomplete list of examples from Slack YVR. Tom Forgacs went to NYC to lead up large enterprise sales. Mike Clapson went to open our APAC HQ in Melbourne and then to SF to lead enterprise sales. Marc Henry went to Toronto to open Slack TOR and lead sales expansion. Kim Graves moved to SF to lead SMB sales for all of North America. Christina Meng moved to SF to lead our Customer Success scale programs. I’m sure I’m missing others who excelled.

Coming back to Slack YVR and seeing all these folks succeeding elsewhere could have made Slack YVR feel like a bit of a minor leagues. Like a branch plant of the actual work happening in bigger places. Like the B team. Like being on the periphery. Yet it never felt like that to me and I don’t think it felt like that to anyone else.

Sure, a lot of leadership roles got vacuumed up by HQ in SF. That happened as soon as Slack started to scale. And certainly lots of folks from Slack YVR travelled down to SF (and to other Slack offices) pretty consistently to drink the coffee, bask in the sunshine, get the good word from on high and collaborate with teammates. But the feeling I consistently got at Slack YVR was that everyone felt really happy to be at Slack YVR.

The sniff test for me that this feeling was legit is that it got talked about not just by the folks who worked daily at Slack YVR, but by the folks who visited from other Slack offices. I heard many teammates from SF or NYC say they went to Slack YVR to get work done. I certainly felt that way. It was quiet, calm and connected to the maelstrom, all at the same time.

Being on the margin didn’t mean Slack YVR was marginal. Rather, I think it meant that from Slack YVR you could get perspective. You were outside the centre of the tech universe in SF or NYC, and that gave you a chance to see a wider perspective for deeper work. The buzz of the newest new thing dulled by distance. That perspective, combined with a historic density of talent and experience, meant Slack YVR always felt like home for me.

And so I returned and started a new chapter of my Slack journey. Back in Vancouver, feeling reunited with home, yet working mostly in San Francisco and New York.

Onwards to EBCs

We settled back into Vancouver and I settled back into a bit of a routine. When I started my 5th job at Slack I mentioned that I faced a pickle of setting — I lived separately from where I needed to do my work. Sure, Vancouver was closer than Dublin, but still it called me to travel.

So every second week or so, I flew down to SF for work. Every 5th or 6th week, I flew to NYC for work. I started to know the flight schedules and found some favourites. I started to navigate the best paths through the airports. I found the decent food options. I collected points. I became that creature of habit and optimization, the business traveller.

Each visit to Slack SF and Slack NYC felt like a snapshot of Slack overall in hypergrowth. That growth drove a kind of strobe light effect to each visit. Everyone at Slack SF was in one office on 5th avenue. Next visit Slack SF was split into 3 offices within a few blocks of each other. Slack NYC had a whole vacant back half of the office. Next visit that back of the office hummed with activity and calls and new faces.

I felt a bit like a stone skipping across the surface of Slack. My new boss Marnie and I started to build out some programs and started to build some awareness of how we could work with the sales team to achieve their goals. We started to create some believers with our EBCs and word started to spread. We educated the team. We promoted what we could do. We tried to be flexible while still sticking to a vision with a clear heading.

And I found I really started to enjoy the work and (of course) the people. But wait — I’m getting ahead of myself again. Let’s leave it there for now.

Up next: Becoming a Senior Technology Strategist — Making up the job as we went. Finding Innovation Tours. Being the Slack man.

And, at the same time as Marnie became my boss, I became the boss of no one. I had no direct reports. Zip. Zilch. Zero.

For the first time since I started building teams at Slack in October, 2014, I just had me to manage. I just had to do my job. I didn’t have to worry about whether my team did their job. I didn’t have to solve anyone else’s problems for them or coach them to find their own solutions. I just had to solve my own problems and do my job as well as I could.

And right away, I felt a terrific lightness with my newfound lack of responsibility. And I felt some guilt at my terrific lightness. Was this too easy? I had habituated to carrying more responsibility. I felt like I should still carry more responsibility. So much remained to be done! And responsibility equaled importance so could I still be important and have an impact?

I wanted to find out and I had put my responsibility down to do so. That change meant I needed to find new ways to conduct my days — way fewer meetings, next to no one contacting me to see what I thought about something. Big changes on the daily habits. I’d be lying if I said I didn’t wander for a small bit of time in those days, finding a new cadence to follow. But then, pretty quickly, work all felt much easier and like maybe I wasn’t doing enough of it.

So what did I do? After a bit of discovery on the job, I realized that just because my role was narrower didn’t mean it didn’t also offer a ton of depth and opportunity for impact. I tried to refocus and do the best work of my life and put my name on the job I did. I pushed my rediscovered capacity onto the essentials of the job and went hard on those essentials.

Essential step 1: get to know the world of Executive Programs and working with Marnie.

What’s Executive Programs?

I know. That’s was my first reaction too. What’s this Executive Programs business? So let’s zoom out for a second and take a quick tour.

By this time in 2017, the Slack sales team was getting close to 150 people globally (a rough estimate on my part, maybe it was 175?) in 6 offices: San Francisco, Vancouver, New York, Dublin, Melbourne and Tokyo. That growth we’d seen in 2 years in Dublin going from 3 to 62 people? Apply that same growth rate to our sales team and you can see how we grew so far and so fast. Slack had been busy already and the rate of growth on the Sales team was about to increase.

As Slack’s sales team had grown it had also gotten more specialized. Direct sales roles had gone from general to specific. Markets got segmented by customer size and geography. New sales support roles slotted in to help our sales process. Now we had folks in legal, revenue management, solution engineering, customer success. Selling Slack had become a team sport, especially with large customers.

We’d also brought on lots of folks with significant enterprise software sales experience. Bill Macaitis had joined as Chief Marketing Officer (CMO) from Zendesk and Salesforce, and Bill strongly advocated for the creation of Executive Briefing Centres (EBCs) to connect with enterprise customers.

EBCs were basically fancy meeting facilities dedicated to hosting executive teams. Sometimes that was a cross-functional single-customer executive team, the CEO, CTO, CISO and VP of Engineering from Airbnb for example. Sometimes that was a single-function, multi-customer group of executives, the CIOs of retailers like Walmart, Target and Nordstroms, for example.

Those fancy meeting facilities were lovely, sure, but what really made the EBCs work was the team behind them — the Executive Programs team. The team I’d just joined. That was us.

We worked as a sales support function, helping sales teams engage their executives, building small events to achieve specific objectives, making it all work. Most of that work happened behind the scenes with preparation and logistics — what I came to think of as back of house from a restaurant analogy. Some of that work happened with facilitation and hosting — front of house. In my job, I found I had to do a little of both.

Executive Programs also ran a few more things for Slack — and we’ll get to those. But the core of the work lived in the Executive Briefing Centres. We knew we’d been successful once folks on the sales teams started talking about ‘doing EBCs’ with their customers as a way to get significant advancement. You should do an EBC, they’d say.

Getting to Know You

Running Executive Programs for Slack was Marnie, my new, new, new, new boss. Marnie was bright and caring and compassionate. She had deep knowledge of the Executive Programs world I was just getting to know, with years of experience working in and then creating similar Executive Briefing programs at other large software companies. She was both reliable and delightful at once, spontaneous and consistent, a rare and charming combination.

I had none of the experience she had and she welcomed me and taught me. It felt like I knew Slack and she knew Executive Programs. So we combo’d up.

The first thing I had to work on was getting to know the new-top-me world of Executive Programs. Marnie oriented her work towards process and loved to get into the details. I had a lot to learn on the big picture of how our work fit into the organization, and then how all the small pieces of our work got done. Salesforce reports, searches and account tracking all gradually became my friends to run the processes. At the same time, I had to create relationships with our sales teams to get to know our customers and find the best ones for briefings.

A second thing I could work on presented itself pretty quickly — public speaking with groups from 6 to 600. Front of house work. Repping Slack to folks who might be interested in Slack.

Closer to the 6 end of that range of folks, some of our venture capital investors ran executive briefing programs too where they showcased their portfolio companies to prospective customers. I could lead those in Europe. We got invited to conferences. I could do those and speak and glad-hand and be the Slack man.

Cramming to the End

Our investor Andreessen Horowitz (a16z) set up briefings in Berlin and I went to meet the CIO of SAP. It was an illuminating first experience.

Top tip, if you meet a senior executive (or anyone you want to have an impact on, really): do some prep. Get to know them. Understand their personal context at their current job. Are they pushing a change agenda or stabilizing things? Cutting costs or expanding? Were they an internal hire or brought in from an external search? Where did they work previously? How long have they been in the role? What education did they pursue and how might that frame their worldview?

Sure, sure, I know you would never show up for an important meeting without prep. You would totally do that research. Right. Except. That’s not what I saw consistently happen.

I kept seeing folks from other a16z portfolio companies meeting the CIO of SAP and it became very clear very quickly they had not done much if any prep work. So just do it. It’ll be valuable to you whether you use it or not and it will make you and your company / product / brand stand out.

If I needed a shortcut model to use, I always used the rule of threes:

1. One thing they kind of already know to establish credibility and show them you’ve done your homework on their context.

2. One new thing for discovery or to surprise or challenge them, built off the first thing.

3. One open-ended thing to give them a chance to respond.

Be ready with tangible examples for them from other customers. Loop back to them what they say to confirm you understand it. Ask lots of questions.

Slack got invited to speak at a design conference in Copenhagen and somehow I ended up going to speak to an audience closer to 600. What did I know about design that I could credibly convey to designers? Near enough to nothing.

But I did know some things about the design process we’d used working on features with customers — the needs gathering and people management and communication work to set the context and then support the design work and launch it to try to make it successful. Let’s call it the work around the design.

So I invited a teammate in our product management team (thank you, Mat Mullen!) to help and we focused on how Slack built, tested, launched and instrumented new features. We showed people an overall generalized process we used at Slack. They we gave them glimpses inside the process for a specific feature to see how everything worked (and didn’t work).

Ever wonder how the emoji reactions feature got conceived, created, tested, recreated, retested and then pushed out into the world? That’s what we covered and it seemed to land well.

Matt played a starring role remotely through short videos and I bridged those videos, setting them up and then joining them together for attendees, then handling any follow up questions. Some questions required me to make a note to get back to folks with a credible answer. Through this tag team with Matt I learned that my new role often was simply to play host and let our talent shine through.

In Madrid we got invited to present at an innovation conference for governments and I partied at the US Consulate. In Paris we got invited as part of LVMH’s Innovation Days to present to their global business teams as part of an internal conference they hosted.

Almost all of these opportunities weren’t direct sales opportunities, but they could lead to direct sales opportunities. They felt like very small scale marketing efforts in closed rooms to mostly exactly the key decision makers we wanted to reach. I just had to be approachable, trustworthy, courteous and curious.

Was it lucky to be seated next to the head of banking innovation at Santander in Madrid? Of course. And then we had a terrific conversation about his home in the Cantabria region, in the town of Santander, where the bank originated, and how hard it was to gather all his family for a week together for Christmas, and how he still loved to cook them all a stew of crawfish, prawns, mussels and clams whenever they showed up.

Learning To Do By Doing

The travel I did and connections I made grew and we started to build a machine to support it. Some combination of the times we lived in and our product momentum and our PR activities and our ability to splash out resources (to answer invitations and coordinate getting there and send someone in person to present) meant we had a chance to have these conversations.

But we had a limited roster of public-speaking representatives. Tier 1 opportunities went to Stewart. No question. He was the star. But Tier 2 and smaller opportunities in Europe, I started to pick up.

It would be too lofty to say that I felt like a missionary ranging out to hostile lands to find new converts. But it also kind of felt like that too, at times. I didn’t face lashing storms or howling wolves or torch-bearing locals. I faced a different slate of engrained beliefs — skepticism, cynicism, conservatism — as well as a general distaste or distrust of US technology.

Yet still, people kept aligning Slack with their innovation initiatives and strategies. People wanted to see new things. People wanted to feel connected to a product like Slack, positioned as the future of work. So, pushing on an open door being easier than one that’s closed, I started framing Slack use as a driver of innovation in two ways that complimented each other. I had stories on how Slack = innovation.

The first way Slack use drove innovation was explicit — through improved work and speed of execution, the classic productivity benefits we could see happening in all our customers. Knowledge work improved with Slack versus email.

The second way Slack use drove innovation was implicit. Slack acted like an internal signal to teams, saying to them that they were expected to work in new ways, open to each other, focused on collaboration, connected to digital tools. Slack showed them they could innovate. Slack had baked-in values that could be smuggled in to organizations to drive change.

And it was convenient for me that both these stories were generally true. Slack did help and Slack did signal. Years earlier we’d seen companies put “…and you’ll work in Slack” as a benefit in job listings. Here were the echoes of that same sentiment.

But here we get to the pickle of setting: most of the work I needed to tackle lived in North America yet I still lived in Dublin and wouldn’t relocate for a few months. So what work could I do to get, as the Irish say, stuck in?

Actually Doing EBCs

Yes, doing the thing. The scary but essential thing I could do from Dublin to get stuck in to the new job was to lead a series of briefings in our London Executive Briefing Centre (EBC).

The full fit out of our London office had been completed and its Radio BBC vibe scaled through the building to our EBC on the mezzanine top (6^th floor). With the London sales team we built a briefing series around the Slack Product Security Roadmap — catnip for large enterprises.

We had our Chief Information Security Officer (CISO), Geoff Belknap, visiting the office and took advantage of his geographic availability to queue up briefings with British Petroleum, the British Museum, Sky, the BBC and more prospects and customers who wanted to meet Geoff. Inside each of these organizations we had a foothold of users and room to grow.

Security, whether our customers had flagged it to us or not, always proved to be a sticking point for Slack use and expansion. It made customers feel uneasy. After all, could they really trust this little startup to handle all their internal communication — jokes and ‘where are we going for lunch’ as well as 5-year strategic plans and ‘here’s why we have to fire John.’

We found through the Slack Product Security Roadmap briefing series, and subsequent ones we ran, that when we led our customers to the security conversation we were way more likely to succeed with the security conversation. When a customer felt like they had initiated the security conversation we had much less success.

It reminded me a bit like taking out a new date as a teen. Asking ‘What time should we be home?’ meant the answer was 11 pm. Not asking or ducking the question meant the answer was 10 pm. Asking for boundaries got us more freedom. Not asking and having boundaries imposed on us meant those boundaries were tighter. We would have never learned so early to seek out the security conversation if we hadn’t stumbled onto the success of seeking it out because we had Geoff in town and tried out the briefings.

And that leads me to this. If I’ve ever found an overarching theme to how I like to work, this would exemplify that theme: Learn to do by doing.

I had to do the thing to really learn how to do the thing. So I got started with what I had, in the place I was, before I could get back home. And that’s another story.

Up next: Back in the Slack YVR — Returning to Vancouver. Resetting with Slack YVR. Getting out to SF, NYC and onwards.

A growing campaign called Together for Yes is building a case to repeal the ban on abortion (that is successful a year later in a 2018 referendum that removed the eighth amendments constitution ban on abortion).

Social change feels prominent everywhere with the general sentiment (in Dublin, at least) that it’s about time. A new generation with a global perspective and contemporary sensibilities seems to be springing forth. The breadth of ideas coming home from the Irish diaspora, the presence of so many folks in Ireland of international origin, the improved wealth and education and mobility of Irish people all seems interconnected to the wider world.

I read a novel like Snow by the great Irish writer John Banville that is set in Wexford in 1957, and Ireland is barely recognizable, like a grandparent in their wedding photos is barely recognizable to their grandchildren.

The perpetual gap between protestants and catholics that infected Ireland for decades as The Troubles and split communities and killed so many feels like a lifting hangover. Sure it’s still there in the inheritances of institutions and in family histories and in stories and in the entirety of the education system. But church is an occasional ritual for most now.

Catholics comprised 94.9% of the population in the 1961 census and 69% in the 2022 census, with only 28% attending church regularly. 26.2% of marriages in 2022 were non-religious civil marriages. The phrase ‘Cultural Catholic’ gained some prominence for its ability to describe folks’ familiarity to Catholicism, though without adherence to its practices. There are churches everywhere but The Church has receded.

I am in London on June 23, 2016 when Britain decides to brexit the EU. People walk around bewildered the next day in the capital. How could this have happened?

When I return to Dublin a day later there is a mirthful glee at the folly of the old enemy and a slighter bewilderment and a small pending question: what could this mean for Northern Ireland? Talk of reunification starts up in pubs and on call-in radio shows and is quickly dismissed. How might we go about doing it now? What could be the reason? Tosh.

In short: lots has happened in all facets of life. When we arrived my son was 2 and splashed in puddles all the way along the street. When we leave my son is 4 and rides a push bike down the back-lane hills. He wants to place his own order when we go for lunch. He insists on including a babyccino in our order at the Ranelagh coffee kiosk we call The Man in the Box.

And At Slack Dublin

The Slack we leave behind in Dublin lives in a different world from the Slack we started with.

Slack Dublin has grown to 62 employees in a new office that occupies a full floor in a glass and polished-metal complex. We walk through metal detectors at the main doors flanked by security guards. We rise among a bank of elevators, members of the mobile phone class, checking notifications while balancing compostable take-away containers. We sit on aeron chairs and eat lunch while working. We have come a long way from Stone Upon Stone Upon Fallen Stone.

Johann has taken the reins and started to run the Slack sales team as he wants. He fits in among the sales leadership immediately and has worked with some of them in previous roles at other companies. The world of enterprise software again proves small and hard-earned reputations travel far.

Quarterly numbers and quotas and territories and accounts pepper conversations as a sales-focused culture rises in prominence. Talk starts about opening additional European offices in Paris, Frankfurt, Stockholm. The business grows and goes on.

After a short time of transition I decline the weekly global sales leadership call that happens at 9 pm local time. Johann is off and running. The business grows and goes on without me.

A Time of Change

We called our performance reviews Feedback @ Slack. I wanted to include some contemporaneously source materials from those days to keep myself honest about the experience and to get some distance.

It is a time of change. By the time I write my own personal performance review (and the reviews of my team) around May, 2017, I see it. Everyone else is going great. But I’m not sure what’s going on with me.

Reflecting on this time and reviewing my notes, I see two stories at once. The first story is full of achievements and facts to support those achievements. We’ve achieved big, hard goals and prospered as we strove to achieve them. Numbers for annual recurring revenues and billings are through the roof. We’ve added new team members in both leadership and individual contributor roles. We’ve done well!

The second story shows up in my notes only in a very muted fashion, and only really at the end. My transition to a new role had been a challenge. I did too much wandering for my own taste, and too much waiting to take on the task of finding my own path. Recognizing my own foundering, I had hired a career coach named Janine who helped a lot. She brought me back to my values and I felt a lot of reassurance from our work. But I also felt a sense of loss.

Looking back I think that sense of loss mostly resulted from a loss of status and clear direction. I had been somewhat important and I had pushed toward clear goals. Now I was less important and had to figure out some new goals. I had been involved in the middle of things. Now I was on the periphery. I had been a part of a team and now I had to figure out what to do as an individual.

I had doubts too. New people had come in and changed how we did things for the better. I wondered: Had I failed? Had I done a poor job?

It’s hard to think so, and yet I did wonder. I’ve tried to be transparent about both my successes and failures. Standards — my own and Slack’s — were high. On balance, I’d like to think my work measured up. And mostly I think I can be satisfied that it did measure up. But still, I regret that it wasn’t a complete win.

I can review the numbers and facts and see the wins. I can remind myself once more that good decisions come from experience and experience comes from poor decisions. I can reconnect with the terrific people I met and worked with. Yet, not captured in there are the small losses. Such is life, I suppose.

Years later I read the following passage from an Irish writer and it strikes me as exactly right:

“You can’t correct the mistakes of a lifetime. You are your own past. These things happened, you did them, you have to accommodate them inside your skin and go forward. Even if you could — and you couldn’t, can’t — there was no going back.”

— Niall Williams, This is Happiness

And so onwards we go.

Feedback @ Slack

“Is there anything else you’d like to add?” is the last question of the Feedback @ Slack form. So many, many things crossed my mind. What could be useful here?

My wife’s wise and excellent voice also crossed my mind saying: Does it need to be said? Does it need to be said by you? Does this need to be said by you now? Right. Suppose not. Once more, onwards.

Instead of any of my half-baked ideas of what I could add, I stick to the facts:

I’ve transitioned to a new role as a Senior Technology Strategist, reporting to Marnie Merriam, and am very keen to get started and completely focused on my new role after completing relocation back to Vancouver, Canada in July, 2017.

So there it is: I’m getting a new job. I’m getting a new, new, new, new boss. We’re going home.

What was a Senior Technology Strategist? And what was Executive Programs? Good questions! I had them as well as I started the role. I had some clues and, better yet, I had a chance to find out. To define what they meant.

When Stewart asked me way back at the start of our Irish adventure in our first All Hands meeting broadcast from Dublin to Slack globally, “You’ve been here opening the office for a few months now, what have you learned about Slack from opening in Dublin?” I said it was the people that mattered most. And it became more true as we lived and and worked in Ireland.

It’s the people that mattered most. It’s the people that made the difference. It’s the people I remember. And it’s the people I miss the most. Thank you to all of them.

Up next — Meet the New, New, New, New Boss: Getting to know Marnie and Executive Programs. Cramming to the end. Learning to do by doing.

A few months before our new product launch Stewart tried out a metaphor with a few folks. The way I remember, it went something like this.

“Did you ever play with Lego and get the platform sheets you could build on? You could join them together to create a grid and they formed the base for what you built? What do you think about using that to describe multiple joined Slack workspaces?”

Hunh. Yes, I’d played with Lego. Yes, I knew the platform sheets. Yes, I thought it could work as a base metaphor to tell the story of joining multiple Slacks.

Oh, okay, I understood after a few seconds, that’s going to be the name of the new Slack product focused on appealing to large enterprise customers. Yes, that could work.

Slack at BigCos

Before we launched Enterprise Grid, it wasn’t like we hadn’t been working with big companies. We’d launched the Plus plan for larger customers in the fall / winter of 2014 / 2015. It included additional security features and controls that our larger customers’ IT teams had been requesting. We positioned it as the same Slack they knew and used and loved, with some added BigCo features to keep IT happy. And it worked well to do just that.

But Enterprise Grid aspired to be a totally different product proposition, purposefully reimagined and built specifically for large customers. Instead of adding features for a single Slack instance, Grid proposed to create an interlinked network of multiple Slack instances, all connected to each other, but also with separate spaces for specific purposes.

We aimed to strike a happy balance between independence and cohesion. You had a small place to work with just your team. You had a big place to work with your whole organization. Maybe you also had some medium-sized places to work cross functionally with other groups too, like project teams, or internal services like finance or HR. And all those various-sized places co-existed within a single Slack Grid.

The Enterprise Grid initiative started in response to three perspectives in Slack’s business that are worth digging into:

1. What existing customers needed

2. What prospective new customers had told us they needed and

3. What we needed as a company

Let’s whip through each of them in order then get to how Grid changed Slack.

1. What Existing Customers Needed

We started using the phrase ‘Champagne problems’ to describe problems we felt lucky enough to have. Our sales leader Bob Frati introduced the phrase and it reached wide adoption because we had lots of them problems.

Growth beyond what a single Slack workspace could really handle? Certainly one of them. We were very lucky to have that problem, yet it still remained a problem for many of our large existing customers.

They had run up against the practical and technical limits of Slack as a single instance. Comcast had 30,000 people in a single Slack instance. IBM had 40,000. No wait, now closer to 45,000. Many other customers had thousands or tens of thousands of people using Slack all day every day. And it wasn’t necessarily a great experience for them. Imagine searching for a colleague among 8,000 colleagues or trying to find a specific channel for just your team among 650 channels. Imagine seeking a file named ‘final-presentation.ppt’ and finding 232 of them. Derp!

Workarounds had been found. Customers started creating multiple workspaces, logging in to each one of them individually and switching between them when they needed to. These daisy-chained workspaces seemed okayish but pretty clunky too. Each needed its own administration, its own user management, its own set up and configuration, its own login in and notification settings and on and on. Lots of small problems grated on people. Some confusion resulted for our customers. The whole enterprise seemed held together with bailer twine and gumption.

And even with really good people working really hard to keep it held together it turned pretty quickly into a bit of a clustercuss that required a lot more work from both us and our customers to keep coherent.

The metaphor that comes to mind here is: Imagine trying to move 400 people from London to Edinburgh, all while working together, and using buses to do it. Each person might get to the destination, eventually, in the midst of gas stops and bio breaks and some missed turns, but what you really needed was to run a train.

2. What Prospective New Customers Needed

We talked with Goldman Sachs who told us they couldn’t use Slack, except they somehow did have many teams on Slack. We talked with Two Sigma investments who were using Slack but on the down low because it wasn’t officially sanctioned. Citadel Securities? Same story. Morgan Stanley? Yes. Millennium? Check.

I started counting and found 65 of the Fortune 100 largest companies in the US were using Slack. We had done an amazing job gaining traction in large customers. Our challenge was to convert that early traction into real, sustained, valuable usage of Slack. See? Them Champagne problems.

We got asked all the time by BigCos, how quickly could we ship them the features they needed to keep using Slack? To expand their use of Slack? We had PayPal as a customer but they restricted Slack use to only their engineering teams, mostly, except they didn’t, actually.

So you get the idea. Our customers needed something different than what we offered them. They needed to keep some of their employees separate from other employees. They needed to track employees for compliance. They needed to know what content appeared in Slack.

In our discussions I learned an alphabet soup of IT acronyms: eDiscovery, Data Loss Prevention (DLP), Enterprise Key Management (EKM), GDPR, SOC, HIPAA, FINRA, FedRAMP.

The phrase “Enterprise Grade” rose in prominence as a catch-all basket for these features, coded with meaning for a narrow and influential audience of CIOs, CTOs and CISOs who had wide ranging powers and mandates to manage software use at their organizations. And, if needed, kill it.

In finance and banking (an industry we coveted traction in) prospective customers described a ‘Chinese wall’ that needed to exist between researchers and traders, for example.

In healthcare (an industry we coveted less but where we consistently found companies seeking us out to help them) information regulation was tight. Patient records needed to remain in patient record systems and not intermingle. They needed ways to track and remove any information cross-mingling.

Government organizations and organizations that worked with governments needed security badges and attestations. They needed to know citizenship details of Slack employees and compliance with export requirements and taxation details.

And on and on. Reality! It has a surprising amount of detail.

3. What Slack Needed

As a company, we needed to keep pushing into new industries as well as deepening our customer base in existing industries. We needed to keep our existing customers happy, meeting their evolving needs and expanding their Slack use.

We also needed to protect the beachhead we’d established and prepare for a world with more competition, especially from Microsoft, who we knew at some point would launch their Teams product.

To someone outside the company that all may seem like the usual capitalist appetites for unending growth. And it was. Land and expand. Customer renewals and annual recurring revenues. Competitive moats. Yes and yes. Blah, blah.

But inside the company it also felt like a natural extension to the path we followed. We did still feel some of that pull of being missionary focused, and venture-funded software was designed to grow as quickly as possible. Our customers signed up and got value from Slack and we wanted to serve them as well as we could.

We still felt a lot of conviction that Slack could be a force for good inside companies, helping them work better together and improving life for tons of people. None of us ever wanted to go back to an email-driven workplace and none of our customers did either (that I can recall or have any record of speaking with).

We still had a feeling that the product we put out into the world and helped people use did truly make their work lives better. Simpler, more pleasant, more productive, as we said. So shouldn’t we try to do that for as many people as possible?

Yes, obviously, was the only answer. But getting the thing done? Let’s just say the expression “the devil is in the details” resonates.

A Declaration of Intent

We launched Slack Enterprise Grid on January 31, 2017, at a splashy livestreamed event. Representative leaders from different parts of our business spoke on stage. We had customers join us on stage too, such as Jeff Smith, the CIO of IBM, saying things about IBM like:

“Teams are using Slack for all kinds of discussion, from delivery to operations. With this, we guarantee that everyone is receiving the same information and it’s all saved for future reference.

…

Collective intelligence will always outweigh individual insights.”

Pretty solid endorsement, right?

But if we peel back the layers of promotion and promise, and get back finally to the values of the Slack product, I think it’s pretty clear the launch of Enterprise Grid was more than the launch of a new product. It was the launch of a different product with different values. It was a statement of intent to our market of BigCos saying: we hear what you need and we’ve built it (or are building it).

New logo and imagery? New product architecture and tooling? New pricing and go-to-market motion and support agreement and uptime guarantees? Check, check and check.

And right, the same great Slack productivity benefits that your employees love. You bet. And values? Well, right.

Two Slack Products and Two Products’ Values

Now flashback to the top 3 Slack product values I covered in part 1:

1. Default to Trust and Openness

2. A Shared Reality

3. Compassion Through Service

And consider, are those BigCo values? I’d say No, Yes, Maybe. No, a default to trust and openness is not a BigCo value. Yes, a shared reality is definitely a BigCo value. And maybe, compassion through service might be, for the right BigCos.

Ask around at a hypothetical BigCo corporate retreat (in perhaps Davos or Aspen or Sonoma) and you might find the actual top 3 BigCo acceptable values would be different, more like:

1. Control and monitoring

2. Risk management

3. Contracted guarantees

And that’s pretty different right?

What I’m getting at is that the system of Slack for Enterprise Grid more closely reflected BigCo values. It didn’t totally overwrite the values of Slack’s original product values, but I’d say it clearly grafted on new values that had to co-exist.

And when there we conflicts, like whether individual users could delete or edit their own messages or change their user names or create a new channel, the BigCo values prevailed. Controls were put in place to centralize all of these options because that’s what BigCos wanted.

Holistic and Prescriptive Technologies

In the first part of this series on the values of the Slack product, we wandered down a pretty academic road with The Real World of Technology, and how that influenced me to think about “the system of Slack” beyond just the application itself.

I’d like to return there now because I think a second concept from the book is helpful to think about how Slack’s product values changed with Enterprise Grid — Holistic and Prescriptive Technologies.

According to Franklin, technology is not a set of neutral tools, methods or practices. She asserts that various categories of technology have markedly different social and political effects. She distinguishes for example, between work-related and control-related technologies. Work-related technologies, such as electric typewriters, are designed to make tasks easier. Computerized word processing makes typing easier still. But when computers are linked into work stations—part of a system—word processing becomes a control-related technology. "Now workers can be timed," Franklin writes, "assignments can be broken up, and the interaction between the operators can be monitored."

My mental shorthand for this distinction is:

• Holistic technologies equal work-related technologies, focused on making a task easier for an individual or team.

• Prescriptive technologies equal control-related technologies, focused on enabling power structures and linear processes.

And I think the best way to think about Franklin’s model of Holistic and Prescriptive Technologies is as a continuum, with a specific technology tending moreso towards one end or the other, rather than as a binary, with a specific technology being either Holistic or Prescriptive. Labels are easy but actually seeing where it fits is hard.

It’s easy to see how the same technology, like the system of word processing in the example above, can be both task enabling and power enabling, and can change over time.

Now look back to the alphabet soup of acronyms that shipped as part of Slack Enterprise Grid and see where they might land on Franklin’s continuum.

• eDiscovery — allows for the legal archiving, searching and discovery of data and its associated metadata (date created, edited, user access, etc.).

• Data Loss Prevention (DLP) — detects and blocks the extraction of corporate data from corporate accounts, for example, sending an email to your personal account with attached company information.

• Enterprise Key Management (EKM) — enables customers to hold the encryption keys to their Slack data so they held exclusive access to its unencrypted form.

• GDPR, SOC, HIPAA, FINRA, FedRAMP — all these are data management standards and controls to meet a the needs of a regulated location or industry or jurisdiction.

All those seem pretty biased towards the Prescriptive or power-enabling end of the continuum to me. Or, put another way, building a product for BigCos meant building a product for BigCo values.

Sure, Slack still positioned itself as the informal, fun, connective app for your team — a reverse mullet of marketing, party in the front, business in the back. But we needed folks to know we also knew big business and we meant business.

How Grid Changed Slack

I don’t mean to sound like a software hipster here, nostalgic for the good old days when Slack was authentic and weird and small and only for the people (fists up!).

Slack grew up and started paying bigger taxes on being different, then realized it was paying taxes on being different and got more conservative to get conservative customers. It became aligned with where it wanted to go. It started to reflect the organizations it wanted to attract, and stopped giving them reasons to say no.

And in doing so, it became much more palatable as a vendor to BigCos and as an acquisition target to BigCos. The product values as they changed over time acted as one clear way to see that change.

With the launch of Grid, Slack moved up market, added features for those customers, dropped features that didn’t fit those customers, and gradually became much more closely aligned with the BigCos. Easter eggs disappeared. Channel management options increased. Administrators were given many surveillance and tracking features. Values changed.

By the time Slack went public in June, 2019, BigCos on Enterprise Grid made up half of revenues. Grid basically doubled the size of Slack and inserted it as an essential tool into the life of BigCos. It legitimized Slack as Enterprise Grade and paved the way for its growth into a billion dollar company.

Up next — An Irish Goodbye: Drawing our Irish adventure to an end. Seeing what has changed. Finding what is next.

More than a few pixels have been spilled discussing the corporate values of Slack as a company, including by me. (See, How Slack Built its Culture: Part 1, Part 2 and Part 3 if you need to reacquaint yourself with what it means to Eat the Goat.)

But those values have (to my knowledge) all been about Slack, the organization, not Slack, the product. And I think it’s worth spending some time on the values of the Slack product, and how they changed over time. So that’s this chapter and the next one.

And to start, a hedge. I know. I’m sorry. This is not a Waffle House. And yet. Here’s the thing: I don’t really feel qualified to write about the values of the Slack product. But I haven’t seen anyone else doing it. And I think it’s an important topic to explore because every product has values, and those values show up in how the product is designed and gets used. In what’s easy and possible in a product, and what’s not. In a product’s defaults. In its character and tone and orientation. In what it enables and doesn’t enable.

I’ve added this chapter to the Dublin section because the values of the Slack product started to become more apparent to me as I was working in Dublin. I think this likely happened for 2 reasons.

First, because I was an outsider in Europe. I was more sensitive to how our product was matching up with different expectations from local customers, employees and contacts. How did Slack get received by UK financial services firms? By German manufacturers? By French software engineers? By Swedish media? It was not the same as the product had been received in the US.

Second, because the product began to change. As we worked with larger customers, key changes happened to make the product more suitable to larger customers, and those changes changed the product values.

For the first 3 or so years of Slack, product changes happened quickly and organically. We grew and rounded out the product in ways we could have good line of sight on. We knew our market well. We were our market. The features we added were features we wanted and could use in our own daily work.

But launching a totally new product called Enterprise Grid in early 2017 meant we had to build a product for organizations much larger than our own, who held different values than our own.

Those two reasons started to cause me to reflect on what we assumed about our product, and how those assumptions at the time needed to change.

(So when I say Slack in this chapter, I’m meaning the product, not Slack Technologies Inc., the organization. Clear as mud? Yes, right, onwards.)

Reviewing The Real World of Technology

Okay, take a second and zoom out with me. To add some additional background context on how I thought about the values of Slack, consider that I’m a person with an English major that somehow got a job in tech. And I felt very at home at Slack, among other liberal arts grads, in what we comfortably called a liberal arts software company. We had a broad grounding in social sciences. Our CEO did a degree in Philosophy. Going down the rabbit holes of humanities is on brand for Slack, so let’s go.

As a university student, I remember darkness came early in the winters. Driving home across the flat white of the snowy Canadian prairies, I listened to a radio series called The Real World of Technology on CBC Ideas.

Ursula Franklin wrote the book and gave the Massey Lectures. I won’t even try to summarize Dr. Franklin’s extraordinary life and career here. Look her up. She’s amazing. And listen to each of the five 1-hour chapters of The Real World of Technology on the CBC website. I strongly recommend them.

Anyhow, key parts of those lectures hit me and have stuck with me. They informed how I saw our work at Slack, starting with seeing software as just a current manifestation of humans integral ability to create tools to achieve goals.

Technology is broader than iPhones and java script and Artificial Intelligence. It’s not just new things that have debuted in our own lives. Technology is also digging with backhoes and sewing with robots and chopping wood with axes and lifting grain with augers and roofing our homes with asphalt shingles. It surrounds and shapes us every moment of every day.

From Dr. Franklin in the lectures:

As I see it, technology has built the house in which we all live. The house is continually being extended and remodelled. More and more of human life takes place within its walls, so that today there is hardly any human activity that does not occur within this house. All are affected by the design of the house, by the division of its space, by the location of its doors and walls. Compared to people in earlier times, we rarely have a chance to live outside this house. And the house is still changing; it is still being built as well as being demolished.

…

In this lecture, I would like to talk about technology as practice, about the organization of work and of people, and I would like to look at some models that underlie our thinking and discussions about technology. Before going any further, I should like to say what, in my approach, technology is not. Technology is not the sum of the artifacts, of the wheels and gears, of the rails and electronic transmitters. Technology is a system. It entails far more than its individual material components. Technology involves organization, procedures, symbols, new words, equations, and, most of all, a mindset.

So technology, in the Franklin worldview, is broad and inclusive, not new and isolated. And our current moment and its technologies are part of a continuum that reaches back as far as humans go.

So when I thought about how Slack was being received in Europe and how Slack was changing, I was thinking about the product in this long-run context. I was thinking beyond just the Slack application. I was thinking about what we might consider “the system of Slack.”

Slack always acted as the front end (software people often call this the top of the stack) of an intertwined system that extended to touch people and how they did things. It included their personal habits and preferences, their self identity and status in a group. It included their relationships with teammates and with their collected work, their reputation, their privilege and access to information. In short, it was a system enmeshed within their overall work systems.

I had always known that at its origin Slack reflected how the Slack team wanted to work. That position held up as part of our founding story. “We all agreed that, whatever we did next, we’d never want to collaborate again without using a system like this. So we thought it might be valuable to other people as well,” Stewart told the Wall Street Journal in a 2015 profile.

But what I think Stewart didn’t say is that Slack the product didn’t just reflect how the Slack team wanted to work. It reflected how they believed everyone should work. The Slack application made an argument for a way of working, for a system of work, reflective of specific values.

Starting Values of Slack Product

Below I’ve tried to specify what I think the original values of Slack were, and then to provide ways those values showed up in the product to illustrate. I’ve limited myself to just the top 3 values I noticed, for the sake of brevity. But there’s certainly a deeper conversation to explore in the system of Slack, with more examples that could include Slack’s Easter Eggs.

1. Default to Trust and Openness

When people first encountered Slack the big thing that gave them pause was its default to trust and openness. The reaction I heard often was, “So, I post something and anyone can see this?” — the tone, clearly concerned; the asker, clearly holding reservations. Yes, that’s how it works by default.

By design, channels acted as the main mode of communication in Slack. Channels were joinable by anyone and searchable by anyone, where ‘anyone’ means anyone logged in to your Slack workspace. Anyone, we assumed, that you worked with. That meant that all work by default was available to everyone else on your team, unless you deleted it, or made the effort to post it to a private channel or direct message.

At the same time anyone could create a new channel, anyone could rename a channel or change a channel topic or description. The default controls for the main mode of communication in Slack were no hierarchical controls. Instead, the default was to trust all the users of the system to be good actors, to let them edit things, and to show who had done anything.

The only real check to this openness and trust was that all messages and actions you did in Slack were attributable to you. There was no anonymous contribution or consumption. If you changed a channel topic to “Stewart sucks donkey d!cks” that would show up as your change. Your teammates could see that you changed it. Transparency and reciprocity in that transparency meant the product held people accountable, and nudged folks so that everyone trusted each other.

Building Slack for trust and openness said to our customers that we believed in them and that they should default to trusting their teammates. They were all trustworthy. Teammates were good actors. And, if not, then you’d find out pretty quickly.

To emphasize how Slack oriented towards defaulting to trust, consider a feature that was not built: Read receipts. Read receipts are those small bits of text telling you someone has seen your message. Slack didn’t have them because we said no nicely as a practice, and what good could they do?

If you wanted someone to acknowledge they had received your message, you could simply ask someone to do so. (“Please give me a 👍 when you see this.”) Having the product tell you someone had read your message, without adding any more value or context, just invited people to create stories in their heads about what was happening.

2. A Shared Reality

With channels as the default mode of communication, everyone in Slack by default also had the same view of the work going on. Everyone saw the channel the same way.

This consistent access and visibility of information contrasted with how people were used to working in email. With email, everyone’s inbox was separate and unique from everyone else’s. In Slack, everyone’s view of the information was common, shared and consistent. Everyone had a shared reality.

To illustrate the contrast of Slack vs email I would often ask folks — have you ever seen a co-worker’s inbox? Has that co-worker seen your inbox? The answer was almost always, “of course not.” Their inbox was like their underwear — private.

But if email was how they worked together, then each person in the organization had a separate, siloed view of the work. There was very little shared reality or context for what was shared, so no one ever knew how much anyone else knew.

Sure, in an email world, sometimes work got shared through CCs and BCCs and mailing lists, but the fundamental model of communication had each participant seeing a different view, and with very little clue to what their teammates saw. Each person was an endpoint in a network.

And people pretty universally hated email. The default settings of “the system of email” was closed communication and near zero visibility between teammates.

And people acted in line with how the defaults of that model worked. Information hoarding, using information for power, lack of clarity on updates, inability to find information, uncertainly on who knew what, did you get the latest attachment? — were these antisocial behaviours because of email or was the design of email because of these behaviours? Yes. There was no shared reality.

Over time we got pretty good at seeing if a team was succeeding or not with Slack based on how much they communicated in channels, or how much they just used Slack like instant email. The more a team posted in channels, the better they performed. The more they reverted to direct messages and private channels, the less value they got from the product.

It was really a great example of how a technology exists beyond the bounds of the product. If a team used Slack like a system of email, they didn’t really work too well. If they used it like a system of Slack, they took off like gangbusters.

3. Compassion Through Service

That’s why what we’re selling is organizational transformation. The software just happens to be the part we’re able to build & ship (and the means for us to get our cut).

We’re selling a reduction in information overload, relief from stress, and a new ability to extract the enormous value of hitherto useless corporate archives. We’re selling better organizations, better teams. That’s a good thing for people to buy and it is a much better thing for us to sell in the long run. We will be successful to the extent that we create better teams.

— We Don’t Sell Saddles Here, Stewart Butterfield

Right from the start, we knew we were asking a lot of our customers. Even if Slackbot provided a great welcome. Even if the sign up process flowed effortlessly. Even if it proved simple as chocolate cake to get your teammates using Slack every day. Even if all these were true — the thing we were asking of customers remained very hard.

So we had to help. Each small step that it took to use the system of Slack, and each small step to improve your use of the system, and to be maximally excellent, we wanted to help. We had to apply to MAYA principle of Most Advanced Yet Acceptable change to every part of our business. And all delivered through a service mindset.

In the product, that meant some guardrails to help people make good choices. Shouty the rooster would warn you if you were about to wake someone up with the notification from your message.

If you ran into problems, that meant we had operators standing by to help out. Type /help in Slack and you could start a new ticket to get help. Email help@slack.com and you could start a new ticket to get help. Tweet to @slackhq and you got an answer. We were asking a lot of our customers, we had to stand up and help them.

And it helped us too. We talked about how we could “maximize the surface area of the company to customer feedback” because the more feedback we could touch, the better we could learn what our customers needed. Customer Support acted not as a cost centre but as a critical contact point between the system of Slack and our customers. We staffed it with very capable experts.

And I’ll tell you a small secret. We sold a specific response time to paid customers. Open a ticket with Slack and you’ll get an answer from an expert human within 4 hours. We had separate queues for paid vs free customers, to triage and prioritize. But we actually gave answers from experts humans to everyone within 4 hours, including customers on the Free plan, not just paid customers.

There were decisions within Slack that felt like they were made because of a principle, even if it was going to hurt aspects of the business, with the idea that being compassionate about our customers, in the long run, was going to make us more successful.

Jessica Kirkpatrick, a senior data scientist, Will Slack Change Work Before Work Changes Slack?

Seeing Changes Over Time

When we started, I think the values built into the system of Slack created its appeal. Be Less Busy wasn’t a statement about task lists. It was a statement about the feeling individuals could aspire to in their work. It was a feeling we hoped to deliver through our product.

Much of the time those values were highly welcomed: more trust and openness in work, a shared reality to rely on, a dedication to compassion through the delivery of a service. But not always. Or, at least, not always as the top values.

“In fact your experience of someone else that you work with if you’re a Slack-using company is often principally via Slack, that’s how you experience your colleagues, most of your interactions.”

— Stewart Butterfield, Stratechery, “Slack Launches Slack Grid, An Interview with Stewart Butterfield”

For pretty much all work places that used Slack, a transference of emotion happened between how they felt about their work and teammates and how they felt about Slack, and vice versa. But as we worked with larger customers, they needed different things and held different values.

What are large enterprise B2B software values? Control, reliability, predictability, growth, security, professionalism. Not exactly matching up to the system of Slack, right? They saw Slack and perhaps wondered if Slack undermined and threatened their control. They liked the promises of the system of Slack — fewer meetings, less email, more productivity. But they had different masters, different values at the top of their list. Some maybe even hated Slack because of what it could represent.

I don’t mean to make large enterprises out to be villains here. They needed to make decisions aligned with their incentives. In defence, openness could be a threat. If you are a telco or utility with a large captured market of customers, you might oppose all change that could threaten your business. Big equals conservative because of the size of risk of what can be lost.

So what could we do? Either we decided to remain focused on organizations who received our product and loved it, and limit the number of customers we could appeal to. Or we adapted the product to find and accommodate new customers, and larger customers, and customers in regulated industries and conservative cultures.

I bet you can guess what option we chose. And that, dear reader, is part 2 of the story.

Up next: Values of Slack Product: Part 2 — Finding what large customers needed. Becoming carrier grade. Launching a new product called Enterprise Grid.

We had also taken quite well to the Irish enthusiasm for leaving Ireland to get some sun on a cheap and easy direct flight south. Our destination: the Canary Islands.

I had loved the idea of the Canary Islands ever since I learned they were the last stop of Columbus before sailing west. They seemed an exotic location, a good distance already away from Europe toward what would be called the new world, yet still part of Spain.

A few evenings of research and we had found Lanzarote, the island of the Canaries we thought best suited our needs. It promised quiet, natural spaces and easy enough access. We proposed the idea to friends living in Bonn, Germany and booked a week to meet up with them.

In our settling in to Dublin we’d also gotten to know our neighbours. On one side, Kiel lived with his rarely seen girlfriend Jess. He swore she existed. On the other side, a young family: Karen and Vincent and their daughters Julia and Clara. Some days we could hear Vincent playing his guitar through the walls. Julia was a year older than our son and he was suitably smitten with her. Realizing this, she ensured she ran the show, choosing the games they played and, as importantly, the princess costumes they would wear.

A few days before we were to depart for the Canaries we ran into Karen and Vincent and Julia and Clara all coming home from the shops in a chatty heap, and they invited us over for an afternoon holiday drink. We had nothing on so accepted.

We made the 10-metre trip from our stoop to theirs and the kids scurried off to play. Vincent asked us if we’d ever had Irish coffees. To us, Irish coffees were fairly mediocre things, often ordered by ladies after church or men at brunch after a night out. In our experience, an Irish coffee was simply coffee with Bailey’s liquor. Often it did get served with a wink, as if to say, this will look like coffee and cream but we’ll know there’s booze in it there, won’t we? But it was unremarkable at its best.

We relayed our Irish coffee expectations to Vincent. He was dismayed. Well, those aren’t Irish coffees at all. How could anything so pedestrian could bear the name? He rose to the challenge. We couldn’t be leaving without a true Irish coffee.

And he delivered. And it was revelatory — rich and savoury and sweet and spicy and boozy all at once. It was so good I have stolen it and repatriated it as our own holiday tradition back to Canada. I made it for the Slack Vancouver office. I make it for an open house we host each year. The recipe I use is below. I encourage you to try it out as your own holiday tradition.

There’s no guarantees, though, mind, that it won’t result in some unforeseen happenings.

That first afternoon when Vincent made us Irish coffees, it ended up turning into an evening quite quickly. The children put on princess dresses and ran around the house as if possessed by banshees, shedding layers of veils and skirts as they went. At some point, bowls of pasta appeared and the children were quiet for 15 minutes. There may have been a charcuterie platter with cornichons.

Much later, after the pasta reenergized the kids, then they burned off that energy, my son came to us. We adults were in mid conversation. He took our hand and led us to the door to get our shoes to take him back to our house to put him to bed. He was done.

My wife tells me she woke at 2 am with heart palpitations from the combination of caffeine and alcohol. I didn’t notice but I did wake up the next morning wondering if I had slept at all.

So, all that to say, I recommend holding the line at a maximum of 2 Irish coffees in a day, and finishing the last one before 2 pm in the afternoon. But you do you.

Irish Coffee Recipe

It may take some planning, but it’s worth it. The perfect time to have an Irish coffee is 11 am on a weekday, with friends. Say, the last Friday before a holiday break, before the kids are home, when you have little of consequence to come the rest of the day.

Ingredients

• Irish whiskey (Jameson will do, nothing fancy needed)

• Whole cream / Heavy cream (~30% milk fat)

• Brown sugar

• Strong black coffee

• Ground nutmeg

Step 1: Whip your cream until it’s firm and holds peaks, about 4-5 minutes. Place your bowl of whipped cream in the fridge with the serving spoon.

Step 2: Make a pot of strong coffee. The best option I’ve found for this is a French press with freshly ground coffee. Let it brew for 5-10 minutes before plunging.

Step 3: Sweeten your whiskey. On a stovetop heat your whiskey in a saucepan over medium heat. When it starts to gently shimmer, whisk in the brown sugar to taste. You want something just starting to look and taste syrupy — about a 2:1 ratio of whiskey to sugar. You don’t want to boil off the alcohol so back off the heat when bubbles start to form. Let it steam on the lowest setting.

Step 4: Make your Irish coffee. Ladle one or two fingers of sweetened whiskey into a mug. Pour over the brewed coffee. Spoon on a generous dollop of whipped cream to cover the whole surface of the drink. Sprinkle with ground nutmeg and serve, optionally with a teaspoon.

Step 5: Adjust your recipe as you and your guests see fit. Sweeter? Boozier? Stronger coffee? Figure out the ratios that work. Keep putting the whipped cream back in the fridge. Maybe hold the line at two. Maybe.

Up next — Values of the Slack Product: Thinking out loud about the values we sent into the world. Reviewing The Real World of Technology. Seeing changes over time.

In the rare occasions when the day-to-day work of just getting up and running gave me a chance to zoom out and reflect on the bigger picture, that question nagged at my brain. Hiring the team and training the team and actually building the business occupied at least a full-time spot in my brain. Years away when we were set to wind up our mission in Dublin seemed years away. But soon enough it wasn’t.

And about a year into our European adventure, I started to get inbound messages from folks. They never said, ‘Hey, are you hiring a new leader and could I be considered?’ They just wanted to meet up, see how our journey was going, share insights on opening up offices in Dublin, learn about Slack. The tone was collegial and friendly, not fishing or transactional.

So I started to meet with some of those folks. Why not? I recognized in them and in our conversations a range of future benefits for Slack. Perhaps we could hire them. Perhaps we could sell Slack to them. More importantly, I hoped we could learn from them and their experience.

These meetings seemed to always take place in rooftop restaurants with large windows, natural light and vistas across the low hiccuping Dublin skyline. These restaurants crowned a selection of fashionable business hotels. In the city centre that meant the bricked charm of Sophie’s at The Dean Hotel. At the Docks, around the corner from Facebook and Google, that meant the sleek minimalism of The Marker. Just off the Grand Canal, a block from LinkedIn and Amazon, that meant The Mespil Hotel.

Starting Work on Chapter 2

The folks I met with approached our conversations with a high degree of transparency and trust, and I appreciated that. So I did too. They seemed genuinely interested in our experience and ready and available to share their own lessons.

They talked about their teams’ composition and go-to-market strategies. I gained perspective on how they hired and grew to their current size. How they targeted specific markets. How they decided to stop working with German customers or French customers or Swedish customers from Dublin and instead open an office in Frankfurt or Paris or Stockholm.

In their stories the second chapter of what we could achieve with Slack in Europe opened up and started to become clearer. Chapter 1 had been landing, finding our feet, getting our first few hires in place and an office up and running, then creating some faith at Global HQ in SF that EMEA was going to go.

Chapter 2 turned out to be building the team from about 30 people to about 120. Getting a newer, larger office to reflect newer, larger ambitions and confidence. Starting to hire beyond Customer Service and Sales to bring on representative business services — Recruiting, HR, IT, Finance, Legal, Facilities Management.

At the same time, it also meant continuing to scale up Customer Service and Sales. Creating a new layer of management in those teams, either by bringing in new hires or promoting from within. It meant creating some segmentation, most likely by market, to reach deeper, develop expertise and serve more customers. French companies liked to work in French with folks in France. German companies in German. UK companies wanted to pay in pounds sterling.

In our journey to decide on opening in Dublin, we’d heard many times the standard stories of US tech companies’ expansion, both from the companies as well as from the team at IDA Ireland. Now we were travelling that path. Some of our journey lined up with those standard stories — our office needs, our hiring progression — and some of our journey diverged — our growth timing proved very fast, we had already opened and hired people in London.

All of this to say: I still had lots to learn from my conversations at those rooftop hotel restaurants.

Prospecting Candidates

The most credible leader I met with was Johann Butting, a German by birth who had lived in Dublin for over a decade. He had deep roots in the web and innovation efforts with Bertelsmann. He had led Sales teams for Google in Dublin. When I first met Johann he was leading Sales teams for Dropbox.

Our meetings always happened at Sophie’s, a vibrant restaurant at the top of the Dean Hotel. We always met at 11am, just as they started service. We both had coffee and maybe sparkling water. The place was empty except for the staff readying for the coming lunch rush, and us. That atmosphere gave us the chance to really connect, without anyone interrupting.

At Dropbox, Johann led a team of close to 200. In our conversations, he had a very strong perspective on how to manage teams and build a business in EMEA. Johann always made it clear he was happy at Dropbox, building the business. But my sense was he also saw how that business was boxed in to further growth. Their core product — synchronized file sharing in the cloud — had been a great innovation that now many competitors with deeper pockets and fuller product lines (Box, Microsoft, Google) offered as well. He could see how Slack’s market position meant we’d be able to continue to grow and really only faced potential significant threats from Microsoft and Google.

In our conversations I should also say that the selling was bi-directional. Dropbox were Slack customers and I wanted to ensure their EMEA leader was an advocate. He was probing on whether our growth and product success was real. I was focused on making it real for him and helping him use Slack more effectively.

We developed a sort of mutual respect for the different parts of the conversation we could have. He could see the trajectory Slack appeared on. I could see his depth of experience and expertise. He could see I needed to speak with lots of people, and our relationship had multiple facets. I could see he respected his role at Dropbox and his team and wanted to honour his current commitments.

Meeting up with Johann felt mildly clandestine, but really out of respect and not out of shame. We weren’t hiding but we weren’t flaunting our conversations. I had visited the Dropbox offices a few months earlier to meet with another person who’d reached out to me and and who we had hired at Slack, so perhaps I already felt like I’d crossed any imaginary boundaries and invaded their space?

In any case, we always arrived and left separately, one before the other, though it was only a 5-minute walk back to the shared office building. I remember standing in the foyer of Sophie’s waiting for him. They had a swing on a rope and the smell reminded me of old ships. I must have been early for our meeting as I daydreamed about the Nonesuch, a ship in a museum I had visited as a boy in Winnipeg. He arrived on time and we both silently recognized we could meet but should keep those meetings discreet.

Oh, and that shared office building I mentioned? Right. That’s because Slack had moved up in the world of Dublin office addresses.

Slack Dublin Grows Up

A key part of starting Chapter 2 of Slack Dublin proved to be finding new offices. We’d outgrown the Guinness Storehouse in more than just floor space. Like with our posh Slack London offices, we knew where we worked could signal our ambitions, and our ambitions had grown with our business.

Our move to One Park Place in Dublin felt simple and easy and obvious. We toured a few other options but leasing a whole floor in the building, overlooking the Iveagh Gardens, beside Twitter and Dropbox who also had whole floors, felt like it matched our trajectory best.

What felt awkward was actually working in the space, at the beginning. Suddenly we found ourselves with room to accommodate around 160 people, though we only numbered 30. Islands of employees gathered in clusters of desks near the windows, surrounded by vast tracts of low pile carpet and empty workstations. It took some effort and time to start to feel comfortable and create a new sense of connection, like stepping into a new pair of shoes. These were still our teenage years so we bought for a proper future fit.

The kitchen, now that we had one, acted as the key focal point. We had meals together. We had coffees together. We started a new tradition called the Small Hands, a meeting for everyone in the office that echoed the All Hands, but just for those of us in Dublin and London. Free massages once a week to go with the free food might have contributed to improving morale and dedicated office attendance. People wanted to be there. We settled in, got to work, and gradually filled the space as Slack kept growing and hiring.

Julian Brophy joined the team from Twitter as a new convert to Sales and took to it like a duck to water. Sarah Hamid made a lateral move from Slack Customer Service to Slack Sales and learned the new job like a star in training. We needed them both up to full speed quickly because our growth continued to make every day feel like a treadmilled race to keep up.

Starting the Search

When we finally formally started a search for a new EMEA Sales leader, I had 4 referrals to offer into the process. Bob Frati, our VP of Sales, was leading the search.

My role in the process? Turned out it was pretty much done. Bob wanted to be hands-on and, though I had strong opinions, I wanted to trust him to run his process and decide on his best candidate. I helped out with those 4 candidate referrals and then went hands free.

It felt a bit strange, but I let go of any notion I had I needed to be key in the process. I had already learned that what we were seeking in candidates had changed. I trusted that we had good people who knew more than me and knew what they wanted.

Mainly, that meant Bob. I joined some of the later interview calls but felt it best to have him come to his own conclusions from the candidates, both that I had met with, as well as the candidates our recruiters had sourced. The successful candidate would be on Bob’s team after all. As my friend Darren used to say, “Hold on tightly, let go lightly.”

For the final interviews Bob flew to Dublin. A packed agenda awaited him. It was his second or third trip to EMEA as Slack’s Sales leader. He landed from the red eye and said he was game to head out for an afternoon Guinness. I can’t remember if we went to Madigan’s Pub on Lesson Street or Hartigan’s Pub on Leeson Lane, but I do remember we each held the line at one. There was still work that needed doing that day. Having the Guinness felt a bit like the warm up, the soft landing, the unofficial welcome to Dublin after getting your passport stamped.

Bob spent the next few days interviewing candidates and getting to know our new office, our new team members. I watched the candidates come and go, including Johann and a few others I had referred to the process and met with. Then things happened outside my view. The process worked its away along. I worked on our daily business with our team. Then Bob spoke with me about Johann. Then Bob spoke with some other folks about Johann. Then we hired Johann.

Johann started at Slack in January of 2017 and that marked for me the beginning of the end of my time in Dublin. Now he was in place. I still had time to help him get up to speed and settled. Then I had to find what I was going to do next.

Up next — Irish Irish Coffee (with recipe): Visiting the neighbours one Christmas afternoon. Including a recipe. Making it to taste.

Yes, we should. And yes, we did, at our Dublin office a few days later. We talked about his experience working with customers to help make them successful with their software purchases, the emerging field of Customer Success. Turned out that when your software product got used throughout an organization, every day from log on to log off, you had make sure your customers used it well. Amen. In short, we hit it off.

It happened that pretty much at that moment we were finding Slack needed Customer Success. Sometimes customers demanded it. Sometimes we suggested with varying degrees of insistence on it. In either case, we needed to ensure that once a customers signed up for Slack, we got to teach to them to use it, use it well and then renew for a lifetime (i.e.: 2+ years in software). So my meeting with Rav proved to be perfect timing.

A few months after our first meeting, Rav joined Slack and started both Slack London and Slack’s Customer Success practice from his kitchen table. He quickly learned about our product and our customers and taught Slack about Customers Success. Prior to Zendesk, Rav had worked at Yammer, Salesforce and IBM. He arrived with a consultant’s background and fancy, capitalized, proper-sounding names for the things that seemed like exactly what we need to do: Needs Analysis, Success Criteria, Rollout and Migration Plans.

Slack London then quickly found real office space in a WeWork tower in Spitalfields, near Bishop’s Gate. Trouble was, this location became the office no wanted to work in. It wasn’t unpleasant or dangerous, but it wasn’t terrific. It was just hard to get to and London was a sprawling metropolis built on a plan of many villages. The commuteless lure of the work-from-home life proved too strong.

The upside to the WeWork space was that we had a corner office with lots of light and glass walls and a view of the reflective cliff faces of similar office towers that surrounded us. The downside was that our glass walls provide zero audio or visual insulation internally, so any conversations from neighbours penetrated our fish bowl, and vice versa.

At the centre of the floor, call booths provided some sound-proofed, padded-wall privacy, if you could book one. The call booths quickly got booked up and people generally stayed home to do their calls. Since calls constituted a large part of the job, the office stayed mostly empty.

That first Slack London neighbourhood felt like a definite moment-in-time highlight for me too. Walking Spitalfields felt like late gentrification. The old market remained and butted up against the new — gritty vendors with temporary tables set up in front of the Lululemon boutique. An Aga showroom displayed ranges costing tens of thousands of any currency, a lifestyle promise of leisure, health, abundance, a modern English countryside fantasy. But reaching their showroom meant stepping over a man with dreadlocks strumming a guitar, his case open for change.

To serve and drive our growth, we quickly created new openings for new people to join Slack London. Rav pulled in Liv, who he’d worked with before, to round out our Customer Success capabilities. She was excellent and salty and very capable. I’ve mentioned how Vic joined Slack from Google and acted as our first Account Executive in London. She capably ran all our UK customers of any significant size (what we called “Enterprise” at the time). Everyone has only three letters in their name until Chris joins as a Solutions Engineer. Now where would we put them?

Moving Up in the World

I’ve also mentioned before that it felt very much like Slack entered its teenage years as we opened our London office. We had decided to be a Sales team and go all in on a really big aspiration. Right-o.

Now we had to do it, and that proved to be fraught with complexities and awkwardness, some searching, some flailing. We didn’t want to lose what we had but we did want to grow into something new. We had fears of what we might become.

Jobs on our Sales team grew more complex and specialized to improve on the depth of expertise we could offer and to free up Account Executives to pursue larger sales opportunities. Solution Engineers helped with the technical and security details. Customer Success Managers helped with rollout, adoption and use. Everyone started using abbreviations for the more specialized roles: AE, SE, CSM.

Did it work? We definitely gained in the depth of expertise we offered to our customers. Our specialists had more specialized capabilities that our customers definitely sought from us. And it proved easier to recruit new employees because now our internal structures and roles reflected those of other software companies.

As a tradeoff, our customers lost the simplicity of having a single person they could contact to solve their problems. It felt like our own gentrification was underway. The edges and corners of our differences got sanded away for efficiency.

The customers commensurately grew as well. The BBC signed on. The government tax collection service, Her Majesty’s Revenue and Customs (HMRC) signed on. The Financial Times signed on. The British Museum signed on to use Slack and agreed to let us use their name for some joint PR. We found ourselves moving up in the old world, climbing the high tea status ladder in London, helped by strong momentum from the Elgin Marbles.

I went to an event at something called Silicon Roundabout (a name no one but bureaucrats and promoters used) and every tech company told us how they used Slack, keen to highlight their custom bot or integration. This customization of Slack for their own purposes made it incredibly sticky. A combination of the product’s many options and the frequency of its use made it a playground for anyone with modest technical skills. They made it their own and felt a sense of ownership over their creations.

Not everything went smoothly though. We did a long sales cycle with British Petroleum and, after many turns of redlined Word documents from their lawyers and security audits and other attestations of our worthiness, they didn’t officially sign on. Over a thousand of their employees paid to use Slack though. They used it for hours every day, then expensed it at the end of every month. But they didn’t sign on, the truism that “time kills all deals” proving true once more.

We did another long sales cycle with Tesco who were in the same situation — lots of people using Slack, paying for Slack, yet no official blessing. They seemed content enough to let the current situation run on at its steady state, and that status quo seemed better for us than forcing a year-long internal Vendor Evaluation process from them. Maybe eventually something would need to be done.

We started to learn how large organizations operated on their own timelines and with their own incoherencies. Perhaps it was an English thing to just keep calm and carry on with such inconsistencies? I’m not sure. Such was life. We pushed on.

Coming To You Live

As our business in the UK grew our team grew, and we quickly outgrew the WeWork office that no one visited. We sought out another office, one that matched our ambitions, matched our desire for prestige and status and our growing capability to pay top-dollar rents.

Touring empty For Let office spaces, I got a chance to see our office options first hand, on a day of tours chaperoned by commercial real estate agents. They started us with some dodgy options, testing our reactions. Gradually the options improved from under construction lofts to full gleaming floor plates.

We reviewed a half dozen options and then met our match, a former BBC Music studio called Yalding House that proved simply too gorgeous to resist. Walking the empty space I could perfectly imagine the emerging version of Slack and Slack employees living in it, thriving in it and fitting in. It felt foreign yet near, gauzy and plausible all at once.

Life at Slack existed at the time in a few different dimensions of time, all of them changing very quickly. Assumptions needed to be updated to keep pace with a newer and newer reality that lived somewhere between the versions of today and an imagined tomorrow. Our new Radio London office space was one of many holy crap moments for me where I glimpsed the further future.

I had flashes of concern for the price that our reach for status would cost. Surely this was beyond our means, no? Much more space than we needed? Too fancy by half? I still felt rooted and responsible to our modest beginnings, getting things to just work. The urgency to make the most of every dollar. And yet.

On those office tours I could see our aspirations come to life, and how an office could symbolize those big imaginings, could project for employees, press, visitors, customers, etc. the class of polished outfit we intended to be. Perhaps we already were? In a world where no one knew anything and everyone was trying to thin slice their way to some sense of what was happening, who was important, what they should bet on, an office address and fit out could provide a powerful clue.

We got approval for the space and cost. The internal enthusiasm built. The fit out went ahead: construction, furniture, decor, signs, details. If we were going to go for it, we decided to go for it all.

The meeting rooms got built out and named after a roster of famous British musicians: Bowie, Rolling Stones, Queen. A dark hallway in the interior featured a rainbow lighting scheme. Walk its length and you passed the full spectrum: ROYGBIV. A black spiral staircase led from our reception to a top-floor mezzanine level that housed our Executive Briefing Centre. Executive Briefing Centre? Yes, more on that later.

We hosted an opening party and invited customers and prospective customers, employees and prospective employees. Slack London now occupied the top 2 floors above Great Portland Street, connecting the thoroughfares of Oxford Street and Marylebone. A rooftop deck surrounded us on 3 sides with views of the BT Tower, the London Eye, the Gherkin. In the lobby a sculpture made of vinyl records showed the audio wave of the last thing said on-air from the building’s former BBC studio tenant.

A listening room lived off the main lobby in another nod to the prior tenants and the building’s former service as the home for BBC Music.

A week after the opening party, I again visited the new Slack London office to do some work and I could see the change: everyone wanted to brave the commute to work in this office. It made people feel good to be there, to be part of Slack, to do their daily tasks in a lovely setting.

Making My Mistakes

Looking back and telling these stories it all seems like a continuous progression, like maybe we knew what we were doing. That’s the nature of looking back. But in the daily moments flying from Dublin to London and back, it felt more bumpy.

To start, I had doubts about my own capabilities. I was in the weeds and failing to get to a high point to stick my head up and check the view. I was unsure what to make of all this change at this pace. I was working as hard as I knew how and yet there always remained more to be done. What was most important?

In my haste and inexperience, I made mistakes. Some of them I saw in the moment. Some of them I can see more clearly reflecting back on those days. Here are three that particularly sting in recollection and hopefully provide some guidance to anyone in a similar situation.

First up, a mistake in etiquette. Our newly minted global sales leader, and my new boss, Bob Frati flew over to visit. Bob and I interviewed Account Executive candidates together. He had sent me a book to read called Who: The A Method for Hiring. We were implemented a new candidate selection method called Topgrading that used an extensive process to group candidates into A Players, B Players, etc. I got the impression that Bob was pleased with the folks we had in roles, and he also wanted to change how we brought in new people.

I remember Bob and I were in an interview with an unremarkable candidate for an Account Executive role. We’d decided beforehand that Bob would lead the conversation and I would take notes. He wanted to train me on how to lead the interview and I needed some practice. Right on. I was keen to learn and wanted to do a strong job with my part.

The three of us — Bob, me, that candidate — sat around a small table. Bob had the candidate’s resume printed and was leading a chronological interview. I was taking notes on my laptop. The purpose of “the chrono”, as we called it, was to review all the relevant roles in a candidate’s work history, from oldest to most recent, and tease out what went well (achievements) and what needed work (development opportunities) in each role. Then we probed to find patterns. The key phrase we used for each role was, “What will your manager say when we call them as a reference?” Not, the hypothetical “…if we call them…” but the definite “…when we call them…”

As the conversation progressed I got the sense that my typing was distracting Bob. After a few minutes he stopped the interview and asked me if I could take notes with pen on paper. Okay, I could do that.

That moment felt like a small mistake and I’m not sure anyone else in the room would even remember it. But it felt to me like a mistake of misunderstanding, like a mistake where I positioned myself to Bob as a person without nuance, insensitive to the context of a meeting and obtuse to how my actions affected others. It felt embarrassing to have the interview stopped and to be corrected.

The second mistake happened also with my new boss Bob, and was also a misunderstanding. But it was less acutely a moment, and moreso a disconnect about how we evaluated candidates and selected people for roles.

With Bob newly in the job, how we ranked the information we gathered on a candidate also shifted. We wanted people with a proven track record, people that had done the equivalent job elsewhere who could be brought in to do the job at Slack. We started to focus about sales quotas, target attainment, on-target earnings.

I got that we were shifting how we hired but I didn’t totally get what that meant to our hiring, and I was slow to change. I was still hiring for the past and present, for the Slack I knew, where I had built the hiring process, where we weighed more heavily the candidates’ performance in the application process than their experience. I was hiring for what I’ll simplistically call character fit over proven track record, because we had thought we were hiring for pretty unique roles and had to find candidates who combined sales acumen with conscientiousness.

Sure we looked at candidates’ track records, but we had succeeded by hiring for character first, and not just transposing someone’s success elsewhere to what they could do at Slack. We talked about wanting ‘Slacky’ people who could do Sales. This emphasis shifted with Bob taking over. Now we wanted Sales people who could do Slack. We wanted folks a bit more mercenary than missionary.

And in hindsight I would have to say he was right to reorient us to track record of success. We’d been successful to that point, but it was another very acute reminder that what got us there wouldn’t get us to the next stage.

We started hiring top performers away from B2B enterprise software competitors — Microsoft, Google, Dropbox, etc. Bob understood the sales organization he had to build. He had seen it done. To be able to scale up and hire as many sales people as we would need to hire, we had to orient toward their proven track record, that scaled and could be uniform. A hiring manager’s judgement call on character fit? Way harder to replicate and standardize and manage.

Did this change mean we didn’t hire great people? Not at all. Going through the list of new employees that joined Slack’s burgeoning sales organization as we opened our Radio London office, I see some of the best folks I ever worked with. It felt like a shift, and the folks that came in felt so strong that it seemed to prove the shift was working.

Yes, it certainly meant our culture was changing too. We had changed our name to Sales from Accounts. Now we started to build a Sales team that could compete with the other top sales organizations in the software world.

(And I don’t mean to beat myself up too much here, retelling these stories of mistakes. We were a teenage company. It was the time to make mistakes!)

The third and most prominent mistake I made during this shift in our hiring approach was in advocating for an internal candidate to lead our UK team. Bob and I had discussions on what kind of person might be a good fit in the role. One of our Dublin employees was a force of nature. They were doing their own job and more. I knew they were ready for a bigger challenge, I just hoped it would be with Slack. I put them forward as a candidate to relocate and lead our London team.

But they didn’t have experience leading teams, or living in London, or leading Sales in the UK. I recognized those limits on their candidacy but I thought they could do the job exceptionally well anyway. Those gaps in experience were challenges they could overcome. They were through and through a terrific culture carrier and a dedicated contributor. I believed they could do the job, learning to do it as they did it, and tackling all the unforeseen things that would arise outside the job description. Again, I was still hiring for character fit — someone ‘Slacky’ that could do sales leadership.

Their candidacy was not moved ahead as an option.

That moment really highlighted for me that I had a mismatch with Bob on what we were seeking in candidates. I was still hiring people for the jobs we used to have, for the company we had been, and based on their track record at Slack. He was hiring people for the jobs we were going to have, and the company we were becoming and their track record outside of Slack.

One of those perspectives was obviously better aligned with time’s arrow, and it proved clearly to be his.

Updating My Priors

As they say in Silicon Valley, I had to “update my priors” to match our new reality. And that reality had snuck up on me and sped past me before I had noticed. I had missed the memo that I had to do different parts of my job in a few different streams of time.

Do I regret these mistakes? Yes. If I’m honest, I do feel some regret about them. I wished I hadn’t made them. But I did. And there are more too.

I showed my own inexperience in these lessons. In doing so, I stumbled at the start of a new, unwritten game I didn’t know the rules to. This was Zork without the user guide. This was executive sales management and I was trying to learn to play while playing.

This game involved status and judgement and ability to deliver results. It involved inferring the smaller signals of belonging and power. I was a noob, learning fast but certainly no threat to set the high score.

I had been in charge of hiring and now I was only a contributor to hiring decisions. I had set the rules for hiring and now someone else had set new rules that I needed to learn. We had operated in our own bubble in EMEA and now we were being pulled into conformity globally to reach scale.

In digging a bit deeper here and trying to unpack what I felt like was really happening at Slack at the time, I don’t want to leave the impression that I was against any of the changes. We had to change.

I believed then and I believe now what we repeated internally: what got us here won’t get us to there (meaning, the next level of size / scale / success). I don’t feel particularly conflicted or like I was coopted. I bought in and supported the changes and was on the bus. I just had to figure out how to get on and play my part.

Did we recognize the bargain we were making? Yes. I think we did. We were a venture-backed software startup with a multi-billion dollar valuation. We had to grow our business to justify it. Growth was our primary job. There wasn’t time to waffle.

The classic thing to wistfully say here is that something was lost along the way. Something lost for financial gain. Some nostalgic element of Slack had to be sacrificed.

And something undoubtably was lost: our naivité, our bubble of independence, the quaint way we thought we could question orthodoxy.

But it’s not like those were things we wanted to hold on to more than we wanted to grow. We wanted to build Slack bigger and strive to reach our potential. We just also wanted to retain some germ of what made us special along the way. And I think we did in a deeply pragmatic way.

We got over ourselves, and any compunctions or doubts we might have had, and we enjoyed the ride. And what a ride it proved to be.

Up next — How I Replaced Myself in Europe: Prospecting candidates. Moving upscale in Dublin.

That travel meant conferences and meetings and events and nights in hotels. Not exactly my favourite, but necessary. The Slack name and our marketing muscles created opportunities to tell our story. Our product adoption in pockets of technology-forward organizations created chances to close new deals, and then expand existing deals into broader adoption. In short, we had to go. That was the mission.

And people wanted to talk with us, mostly. We still encountered lots of skepticism overall, but we started to see through that resistance to find the places we could have an impact. I met with the nordic media house Schibsted and they wanted to upgrade to 1,500 people. Barclay’s had a digital division using Slack that wanted to expand. Spotify was growing from its fledgling Stockholm roots and Slack acted as their global digital communication hub.

We started to learn how Europe wasn’t really a market, roughly the size of the US. It was instead about 20+ smaller markets, each with its own nuances and wrinkles and restrictions. Each also with its own digital leaders and progressive organizations.

So we started to carve off markets to focus on. At the top of the list we found the UK and Ireland, Nordics in Sweden, Norway and Denmark, maybe the French or Germans, if they fit into tech-led industries. But beyond that? Not a focus for us at the time. If customers came to us we’d certainly be happy to help them. But we stopped thinking broadly of targeting all markets, and we started to be selective.

Onwards to London

First up: jolly old England. We opened a temporary office at the WeWork Spitalfields in London. Our Customer Success expert Rav occupied its glass, fishbowl space most days, and it promised to house future boots on the ground in the world’s second largest software market. We got settled and quickly hired Victoria as our first dedicated Account Executive and second Sales team member in London.

I learned the flight from Dublin to London was the busiest single route in the world. I ended up flying it most weeks for a few months, then every second week as we got up and running. Did I want to fly into Heathrow or London City airport? Depending on the traffic, the meetings, the time of day, the weather, that question and many other travel optimizations started to occupy a consistent corner of my mind.

My London days got divvied up between customer demands and internal needs for hiring, managing, training. We visited Sky News and learned they had integrated Slack into their live news-gathering and broadcasting workflows. We visited the online grocer Ocado to see how Slack helped them pick and pack groceries across their dozens of warehouse before the crates went out for delivery on their fleet of vans. I dug deep into their specific examples and felt amazed how all these folks had taken Slack and made it work for them in ways we could have never imagined. Once more, the value of talking with customers (and mostly listening) shone brightly.

On the hiring front, progress was clear as a spotted dick. Victoria arrived perfectly prepared to hit the ground running and act as a culture carrier in the fledgling London office. Excellent. Then things clotted up.

I interviewed a candidate for a Sales role who basically admitted to fraud (pumping up fictional user numbers just prior to a software license renewal) when I asked him if he’d ever had to lie at work. That put a stop to the interview. Competition for top sales people proved challenging and we had to slog through a raft of highly variable candidates to find winners.

Cardiff and The Future

We started to see some progress with customers. After a day of work in London I took the train to Cardiff to meet with a team at General Electric (GE) responsible for their internal tools. They were already using Slack and wanted our help to position it as part of their overall approach to work.

In introductions at our first meeting, the GE folks mentioned their respective tenures at the company: 16 years, 22 year, 26 years. GE was founded in 1892 by Thomas Edison. Slack had a commercial product in market for less than 30 months at the time. We came from different worlds yet met in a good place.

The GE folks wanted to drive change. They shared with me a slide demonstrating their internal tools strategy. A table listed Slack along with Google Apps, Confluence and SharePoint. Slack’s label? The Future. Could we ask for much more at this stage? Capital F future. Our positioning seemed to be working.

The meetings fell during the 6 Nations Rugby tournament, the Cardiff shop windows festooned with blazing red jerseys supporting the Welsh national team. I bought a dragon coffee mug for home in Dublin, a rugby jersey for my brother back in Canada and tried to pronounce Cymru.

TechCracker at Stirling Castle

I flew to Edinburgh with my family and we drove to St. Andrews for a conference called TechCracker put on by one of Slack’s funders, Horizon Ventures. We arrived a day early and spent our free time walking St. Andrews: the picturesque streets, studied academic vibe since 1412, the Old Course where golf originated, the cafe where Will and Kate went on their first date.

At the conference, the Horizon Ventures portfolio companies set up booths to demo their products. Many are software products and I’m familiar with their demo process — questions that lead to the problem, workflows that lead to their solution. Others are much more exotic and research-intensive tech like cultivated meats, fermented milk proteins, virtual reality. I ate a cheeseburger of grown, ground ‘meat’ with grown, cultured ‘cheese’. They tasted fine, though different. Pretty much all the companies already used Slack so my role ended up being focused on answering product questions and helping them improve their use with tips and easter eggs.

Scottish First Minister Nicola Sturgeon opened our first morning of the program with a welcome. She talked about Scottish innovation and invention and the Scots openness to the world of technology. Her handlers snapped some photos and hustled her in and then quickly out again.

In our small talk backstage after she’d spoken she asked me how I was enjoying Scotland. I told her it was my first time visiting, and as soon as I landed I could see how so many Scots felt very at home in Canada. “It feels very familiar.”

“Do you have family from round here?”

“My grandparents sailed from Dundee to Canada in 1905.”

“Well, we have a lot of tourists that come to Scotland looking for their roots. I’m not sure they’re always pleased to find them.”

And with that she gave me a look as if to say, “I’m off,” nodded and she was gone.

That evening the conference organizers took us by coach to Stirling Castle, which they had rented for dinner. We dressed for a James Bond theme. A pipe band welcomed us as we disembarked. We were shepherded through the empty castle and into a Great Hall for dinner at long tables under purple lights.

At a quiet moment I felt a bit in need a recharge and headed out for a walk through the castle. To my surprise, I could keep walking, everything in the castle open and accessible. I self guided a tour through the halls and rooms that saw 600,000 visitors a year. The castle was resplendent with heraldry and unicorns and plaques retelling stories. I lingered in the royal bedchamber and stood where Mary, Queen of Scots was crowned in 1542. Beyond the walls I read about where King Robert the Bruce won the Battle of Bannockburn against the English and inspired the unofficial Scottish national anthem, Flower of Scotland.

The Techcracker conference carried on. I rejoined the group and tried to play my role as Slack ambassador as well as I could in my rented tuxedo.

I flew to Copenhagen for another conference. We met with Maersk and learned how they customized Slack to track all their ships sailing the globe and receive notifications of route changes, weather alerts, news bulletins and more in one place. They called it their digital control tower and told us they used Slack more than any other software tool. Yet they had security concerns. Could we dig in deeper? Certainly.

I flew to Paris to present to Atelier BNP Paribas, their innovation organization, the offices housed in a magnificent building. We entered and passed through layers of security before descending through ornate vaulted ceilings to bland beige meeting rooms that could have been the basement of any global bank.

I tried to keep learning new things at each stop. The Atelier BNP Paribas meeting stands out because its the clearest example of the clear allure and danger of Slack’s positioning as a catalyst for innovation in large organizations. We met with their innovation group. Our message resonated with them and they were keen. Great! That was the clear allure.

But then, a downside of being a catalyst for innovation emerged. As we got deeper into the deal we realized being a project of the innovation team meant being considered a toy product, not ready for enterprise adoption, potentially just a trifle really, a passing fad. We got some traction but it proved to be down a dead end road. Every large organization had an innovation division or lab keen on Slack yet only sometimes taken seriously in the larger organization.

Yes, Sure, Right, But

On the business front, through all of these trips I found an overriding theme emerged for Slack embodied by the phrase, “Yes, sure, right, but.” It was partially skepticism about a US tech company, and partially slowness to adopt new technologies and partially the lack of an overarching narrative of change and progress inside most organizations. They were curious and adrift. We kept hearing that our vision of the future was better than their vision, and their present, yet organizations still clung to the inertia of their past decisions.

On the one hand, I appreciated that the folks I met had pride in their traditions and a reticence to move too quickly to adopt anything that seemed to be growing so quickly. As if saying, “this thing called Slack has become something so fast, it certainly also become nothing just as fast. We will go slow and see what works for us.”

On the other hand, there was concurrently a deep insecurity about missing out, about being slow, about being left behind. Much like a younger sibling, they were worried about missing out. They felt they’d missed out before. They wanted to play too. They could keep up. They had their own software success stories and tech hubs and research universities and business successes.

This contradiction of, “Yes, sure, right, but.” meant we did well with our business expansion in EMEA. But we didn’t do as well as our teams in North America. We grew, but not as fast. We closed new customers, but not as many or as large as in the US. It took time to do the thing and to do the thing for the first time.

I’ve mentioned before how the US has a huge inherent advantage as a location to start a software business: a single currency, a single language for business, a huge number of customers, tech hubs and a entrepreneurial culture and funding structure to continually mint out new startups. But the largest of all the advantages the US enjoys is its culture of openness and optimism. Failure can be a badge of pride, not shame.

When presented with what we were selling at Slack — a vision of how to work in the future — the default US response? Cool, yes. We want that. It’ll be great.

The default EMEA response? Yes, sure, right, but. It was the but that stood out, that slowed or stopped conversations, and we had lots of work to do to navigate beyond it.

Taking on the Mission

I flew to Oslo for a jam packed 2-day itinerary, followed by some personal time. As I mentioned earlier, as I traveled more I started to combine some of my trips with personal time so my family could join me.

During the days and many of the evenings, they did their own thing as I worked. Then we usually added on a few days of family time in a destination before returning to Dublin to resume normal life.

In Edinburgh we found a fun fair and my son rode a burlap carpet down the slide of a helter skelter like he’d seen in Peppa Pig cartoons. We rented bikes and rode the paths of Copenhagen, discovering their wonderful playgrounds built into parks and forests. We lazed on the spring grass of Oslo’s Vigeland Park with a picnic and marvelled at the granite sculptures of humans in every stage of life.

The travel inherent in the mission proved to be both exciting and exhausting. New places, new people, new experience all kept me going. Learning kept me challenged. Raised in Canada with stories of explorers and the Jesuit Black Robes I felt a sense of exploration to my own experience, a sense of going out into the world to prosthelytize a new message. I don’t want to overstate this feeling, but arriving in a new place I definitely felt I was representing Slack. And there was a duty to show up and represent well and pursue the mission.

And it took a toll. I don’t expect anyone to feel sorry for me when reading this. I was incredibly lucky every day to get to work at Slack. Every day I felt a ton of energy getting to do what I got to do.

So I say that it took a toll as a cautionary note to anyone else who might be considering or supporting someone on the same path. It can be hard and it can require sacrifice and some self preservation tactics. A social scientists would call it a greedy job — one that soaks up as much of the time and energy it can from a family’s life. And it wasn’t a surprise.

When we decided to leave to Dublin we certainly knew we would be making sacrifices. In this period of intensive travel, we had to imperfectly deal with those sacrifices while trying to protect the most important things: our time together, our connections to each other, the primacy of our relationships as a family.

So when I say my wife is the brains of the operation, I’m not being facetious or glib. That mission I had to take on? It wasn’t just my mission, it was our mission, and I couldn’t have done it without her.

Up next: Gentrifying Slack with Radio London — Moving up in the old world. Coming to you live. Making my mistakes. Updating my priors.

This was Stewart, asking me for my opinion on the sales leadership candidates we had been interviewing. We had finally posted an opening for a VP of Sales at Slack. But the role felt like a hard one to fill. Let’s dig in to why.

First off, those of us leading Sales at Slack — myself and AJ — had to do a bit of pride swallowing and decide that we could not do the job. We didn’t have the experience. We didn’t have the skills or the vision or the capabilities. We covered that last chapter in Leaving Never Neverland.

Our pride swallowing completed, we decided we could see the bigger picture. We needed someone who’d done it before. We needed someone who could teach us. To get to this realization actually proved not too hard because as soon as we got into any specific detail of execution — Who were we going to hire next? Did we segment by industry, geography, customer size? How did our compensation plans need to change? — we could see we’d be quickly out of our depth. And now we got to hire our new boss. Great! But we didn’t come at the hiring job without our own respective ideas about what we needed.

Secondly, the Slack of 2016 was only 2 years into having a commercial product available and many parts of the organization still felt very development-driven. “Doesn’t the product just sell itself?” was a question I had answered many times to internal folks who saw the success of some of our product-led growth. Why did we need sales people?

Our CEO had even been quoted in the press saying no salespeople for us. So you could perhaps have the impression that Slack maybe didn’t feel totally sure that it even wanted to be in Sales. That would have been accurate. So we needed to do a bit of a sell on Sales internally. That effort happened in the midst of many coming-of-age efforts to evolve Slack into the company that could seize the opportunity we faced.

Is that a company you would have wanted to join?

Feeling Our Teenage Years

One of the phrases we used at the time to rally around and edify ourselves was “What got us here won’t get us there.” Meaning: what we are doing today is a result of what we had done in the past. And that needed to change because we had new goals in a conceivable future.

The phrase basically acted as a reminder to not be too wedded to the past. We had to keep learning and keep letting go to be able to adapt to the new lessons. We had just started to glimpse what we could become.

Another phrase we used to drive home the need for consistent openness to change was from Molly Graham: Give away your Legos.

“People think, ‘Oh, that person joined! Now I can finally work a little less.’ But that’s almost never what happens,” Graham says. “Adding people is the opportunity to find a new job (or the new version of your old job). But this requires individuals to freely give away parts of or sometimes all of their old job — handing over projects, programs, products, code that they probably built from scratch. It means trusting other people with something you care about.”

So we were evolving quickly and trying (trying!) to do it thoughtfully. And it felt hard and weird and scary, like it always feels outside your comfort zone.

We had already started to move beyond the old joke that Slack was the perfect product for Slack the company. Our development organization had needed to evolve to serve larger customers. They had needed to bring in outside experience and expertise they didn’t have and didn’t have the time to acquire so that Slack as a product could scale beyond just Slack the team.

Now our Sales team needed to follow a similar path and evolve so that Slack could be sold in ways we didn’t yet know how to sell. We needed to grow up. But we didn’t necessarily know what that growing up looked like. And it all felt like it was happening very fast.

To put it into human terms, Slack felt distinctly teenage in its journey, especially in our sales teams and functions. We had some capabilities. We were closing large deals and the Wall of Logos on our website and in our slide decks kept expanding with recognizable, high-value names. We had tons of opportunities knocking on our door and new ones came in daily.

But we didn’t have anything resembling a mature, pro-level business-to-business enterprise Sales game. No customer targeting to get the customers we wanted instead of just the customers reaching out to us. No territories for different sales people to own and build out. No quotas to work toward.

Our Sales team consisted of a few managers who did some coaching, a few Solution Engineers who handled technical conversations, one Customer Success expert and a whole lot of Account Managers who handled all parts of customer inquiries, helped by our support team. Somethings had to change. We didn’t necessarily know what those things needed to be, but we knew we needed someone who did know.

So to get back to Stewart’s question that I opened with — “So, who are your top 3 candidates?” — is to jump right to the middle of our process to find that person to help us evolve in Sales. Stewart was running between meetings when he fired off that question to me. I had just landed following a 9-hour flight direct from Dublin. Perhaps my filters were a bit porous so my answer had next to no nuance.

“I don’t have a top 3,” I told him. “I have a top 1.”

That top 1 was Robert Frati. Everyone called him Bob.

Interviewing Candidates and Bob

The interview process to find a VP of Sales had been a bit long and a bit fraught. We had been hiring in our Recruitment team, so we had some inhouse muscle pushing ahead the role and lining up candidates.

From those dozens of candidates in the pipeline I personally spoke with about 12 whenever transatlantic hours sync’d up. These candidates all had very impressive titles and backgrounds. They were polished pros. VPs and SVPs and EVPs and CROs from established software leaders like Oracle and Salesforce and Google and Salesforce and Box and Salesforce again.

(Oh, Salesforce. They get repeated on the list because we interviewed a lot of people from Salesforce. Mostly what we learned is that they had a ton of people with very inflated titles, a tactic I later learned seemed geared toward getting customer meetings with prospects at the most senior levels possible. Maybe also to reward folks with titles that cost very little versus money that cost money.)

These candidates knew us, kind of. In the preceding quarters Slack’s profile had been growing. That meant we had some capability to interest external executives. A virtuous cycle spun up around our story. Each round of fundraising meant more people knew us and more customers signed up and more candidates wanted to work at Slack and more stories got written about Slack founded on actual success. Etcetera.

But that hype cycle only got us nibbles with most of the senior executives I met with. They were interested, sure. They want to stay up to date. They wanted to know more about the new, new thing. But they were also conservative and comfortable. To use the analogy of bacon and eggs (the chicken is interested, the pig is committed). These were chickens.

Hiring Our New Boss

I flew the direct Dublin-to-SF route, over the wrinkled ice of Greenland, for a regular check in with HQ and meetings. In Dublin the effect of our hype cycle felt muted but still real. Perhaps 6 to 12 months lagging the US. In SF the hype cycle felt amplified and like it could spin out of control any moment. It was almost untouchably H-O-T.

At the 11th hour the goal of my trip narrowed to a single priority — to interview Sales leadership candidates. Maybe decide on one? Maybe decide on one. Our excellent recruiters had worked really hard and lined up the conversations in successive blocks on my packed daily calendar. And I’m sorry to say they proved entirely forgettable.

I’m not saying these conversations felt hard. Nope. All the interviews went fine. The candidates wanted to have a conversation with us. But they mostly also played it cool. Sure, we could talk with them. We might be able to sell them on joining Slack. Maybe, but did we know about their awesome current job? These were popular kids in demand to go to lots of parties. Why attend our party when it meant giving up on a party they already knew was awesome?

At least, that’s how it felt interviewing them. The only candidate interview I remember was Bob’s interview. He arrived on time. He arrived well prepared. He’d even researched those of us he was meeting with (me and Allen and AJ) and had talking points for each of us. First impression: much better.

We met in one of Slack’s larger meeting rooms. Bob set up to replace the emoji clock on the screen with a presentation from his laptop. He told us his story.

At the time, Bob led Sales for Salesforce throughout the Asia Pacific (APAC) and India region. He was originally from Northern California and had tons experience selling business-to-business enterprise software.

Bob used a presentation software called Prezi to introduce himself. The overall metaphor of the presentation was a journey. It started with a zoomed out view, a map of the world. We could see on the screen the arcs of travel and destinations of the trip he wanted to take us on. Then Bob zoomed in on key times: where he started, his background, his personal life, some formative experiences that acted as symbolic of his approach. He showcased what mattered to him.

He’d worked his way up through 10 years at Salesforce, starting as an individual contributor with a quota to hit before becoming a sales manager with larger and larger teams of individual contributors with quotas to hit reporting to him. By his experience, he seemed seasoned enough to deeply know the orthodoxy of software sales. By his interview with us, he also seemed flexible enough to learn what had already worked for us and to create a path forward to scaling.

He made some guesses and then wanted to learn more about what could make him successful at Slack. Sure, he also told us a bit about how awesome his current role was, but that was secondary to what he told us about the team he ran, the culture he’d built and the people he’d worked with. Like with all the best folks we hired at Slack, interviewing Bob felt like a mutual, reciprocal journey of learning.

It was refreshing and was the reason I told Stewart he was my top 1 candidate. The other folks we’d interviewed had been fine, but they hadn’t shown up to the conversation ready to learn with us. They’d show up ready to showcase themselves and perhaps be convinced to go any further. Bob had shown up to meet us, learn with us and win the job.

After Bob’s presentation we had a chance to ask questions. Here are my 5 questions from that interview:

1. If Slack is bankrupt in 3 years what most likely went wrong?

2. What do you get credit for that you don’t really deserve?

3. What do you know a lot about that I know nothing about that you can teach me in 3 minutes?

4. Why are you considering leaving Salesforce?

5. What’s the hardest thing you’ve ever done?

Bob did well with all of them. Where he had insights to offer, he shared. Where he had stories to tell, he recounted them. Where he had questions, he asked them. Where he didn’t really know an answer, he said so.

Some additional meetings happened between Bob and Slack. I’m sure he met with Stewart more times. He must have met with Allen again. Everything progressed in the background and I heard one day a few weeks later, back in Dublin, that we had made him an offer to join Slack.

I remember an odd feeling at the time of the juxtaposition we held in our business. We had achieved excellent growth and had more excellent growth directly within sight. The wins had started piling up and started to feel like good evidence of what we were doing. But we also didn’t really feel like we knew what we were doing. We doubted and pushed on.

Maybe we’d just lucked into all this success? We had systems and ways of doing things, but we only had our own experience to prove that it all worked. It felt like at any moment someone might turn on the lights and tell us kids to quit playing at Sales. The adults will take it from here. Like it mentioned, these felt like our teenage years.

Bob became my new boss and shifted the trajectory of our company. He didn’t do it alone. He didn’t do it all at once. He hired other very excellent senior leaders to help. He made changes and reacted to what we saw happening. He didn’t have all the answers either. He listened and grafted a plan together to build on our existing strengths and successes. It wasn’t a day-and-night change, but his hiring signalled a significant change for Slack and for Slack Sales in particular.

So we’d reached a new point in the story. We recognized we could be really big, and we recognized we needed new people to realize that ambition. Now that we had one of the key people in place to start that new part of the journey, how far could we go?

We didn’t know. But we were going after big customers and we going to try to be as big as possible.

Up next — I See London, I See France: Getting beyond Dublin. Onwards to London, Paris, Cardiff, Edinburgh, Copenhagen, Berlin, Oslo. Taking on the mission.

Maybe we had to grow up? Okay, definitely. Eventually. At some point.

At first, I confess, I felt pretty hesitant to accept that we needed to grow up. What did growing up mean? Two big things right away: external leadership with more experience and what they could bring — a more conventional business-to-business software selling approach.

I dawdled and dragged my skeptical heels. Hadn’t we done pretty well so far? Shouldn’t we keep tailoring our work to our product and market? Learning as we went? Inventing what we needed? Instead of adopting the conventions of the industry? Was it maybe me that was stuck in a Peter Pan world and not wanting to grow up? Maybe, maybe?

Okay, yes. We needed to grow up and move up market into larger deals. Our customers were pulling us there and we needed to scale our sales organization. We needed folks who had done this thing before and learned the lessons, and I was scared of what that might mean. I kept reminding myself of the classic I’ve mentioned a few times lately: good decisions come from experience and experience comes from poor decisions.

So I had to get out of our way. We needed to bring in some experience because we didn’t have time or latitude to make the poor decisions and gain our own experience. When faced with 10 options of what to do, we needed folks who could point to the leading 2 or 3, and then help us decide between them.

We needed to recognize that what got us here wouldn’t get us where we wanted to go.

Growing Up and Growing Apart

Just as we hadn’t reinvented Accounting or Recruitment or IT to suit our needs, we needed to remember we didn’t need to reinvent Sales to suit our needs. Even if we had started out believing we wanted to reinvent it. Many large B2B software companies, like we hoped to become, had already been built, and they pretty much all looked the same.

If we aspired to follow their path (and we did) then we needed some shortcuts. We just had to get over ourselves and our own success to see the lessons we needed to learn. (That last sentence might as well read, I just had to get over myself and my own modest success. The things we had built and that had worked so far could also constrain us in the future.)

So we did what all technology companies did to make a decision. We called an offsite. It felt about right timing wise anyway. We had kept hiring at a quick pace and we needed to anticipate that our pace would only increase as we kept succeeding. New people meant new ways of doing things. Change was coming and coming fast. We were ~20 people and going to be double that and double that and double that again soon enough.

As we readied for the offsite we scoped out what we wanted to achieve. AJ and I spent time on calls building agendas. What did we need to do?

• Get the team together. Actually see everyone in one place for the first time. We needed to humanize everyone.

• Introduce new team members. So many had never connected with each other. We needed to create bonds.

• Figure out our mission as a team. Get some words to describe ourselves and our mission. We all needed to pull in the same direction together.

• And lastly, answer the biggest elephant in the room question: were we an Accounts team or were we Sales? We needed to decide on an identity.

The question of whether we were Accounts or Sales felt important at the time. AJ and I had batted the question back and forth. He came from a Sales background. I came from a no-Sales background and feared what going all in on Sales could mean: finger guns, jumping on calls, cutthroat quotas and stack-ranked leader boards.

Looking back (and perhaps looking in from an external perspective) it seems like such a fine detail to focus on. What a trivial bit of precious self indulgence — Sales vs Accounts! But the question of our team name also acted as a signal of an internal question we struggled with about our purpose. Did we exist to help customers use the product and maybe do some commercial business? Or did we exist to do some commercial business and help customers use the product?

And perhaps you read that last sentence and thought, what’s the difference? Get over yourselves and get on with it. It can’t matter that much. And I get it. It is a bit of Silicon Valley myopia. A foamy latté problem (“My la-tay is too fo-may.”).

But I’d defend the question of Accounts vs Sales as a moment of navel gazing that actual led to better team work, simpler hiring and clearer internal incentive systems. It helped us answer key questions. For example:

• Do you move to an industry-standard variable compensation system that rewarded deals? If so, how do you balance base salary versus variable compensation?

• What roles do you need to create on the team to reflect your team purpose?

• How do folks get reviewed and promoted? How do we hire? Who do we hire?

All those questions hinged on our purpose as a team and the team name reflected our purpose.

So, all this to say, at the time the name of our team did feel important. Important enough that it got its own session in the offsite and still sticks with me as the most vivid question we had to answer. It held all the tension leading up to the event.

And that tension reflected our team’s evolution. As we’d grown and added people to the team in North America, we’d already started to add new roles. At the start, the Accounts team consisted entirely of Account Managers responsible for all the questions that any customer that walked in the door could have. All Account Managers acted as a single point of contact for the customer to answer all their questions. But then we couldn’t answer all their questions. We had found our own competency trap.

Competency Traps

As our deal opportunities and customers got bigger and more complex, our “everyone is an Account Manager” model started to show some cracks. We had gotten very good at working with tech teams inside larger organizations, and with smaller and mid-sized technically-minded organizations.

And our Account Managers were instrumental in this success. Customers really liked to have one point of contact to help answer their questions. Our Account Managers liked to be experts and to be able to marshall their portfolio of skills to answer those diverse questions and be the single point of contact. It worked.

But in larger organizations, we struggled to succeed as much as we could. And with more traditional organizations, we struggled to expand beyond tech teams. Our Account Manager generalists were pulled in too many directions. Our customers grew more complex, more conservative, more passive about solving their own problems or even asking about them.

Plus, the supply of Account Managers felt very thin. Finding successful candidates with the range of skills and experience necessary to fill the role proved challenging. Customers loved to have one point of contact. But we were learning we couldn’t train that single point of contact to be an expert on everything. We had reached the limits of the model.

Matching Our Customers

What we needed to see is how we needed to start to match our customers in all the ways they expected. We needed to bring in mid-career and senior folks to sell to larger customers and to sell more complex deals. Okay, right then. So what did that mean?

Those mid-career and senior folks were used to living in a larger Sales organization, supported by many specialists. They had titles like Account Executive. They had territories and industry expertise and quotas and contacts and travel allowances that fed into travel rewards programs they used for their personal vacations. When we interviewed one of these folks it felt very different, like we had moved from the junior school playground to the senior school locker room. This was a new game. We didn’t know the new game well, but we still found ourselves playing it.

The first additional role we hired was Solution Engineer for deeper technical expertise. Kevin Albers joined the team and got to work on the implementation details for Slack, like security questionnaires, Single Sign On (SSO), authentication and API integrations. Our demos for customers started to include Kevin riding shotgun to handle the technical details. Customers liked that. It matched what they expected. And it proved handy that Kevin’s expertise on the calls accelerated deals for our larger customers. Yes, please. I could see perfectly how that was a winner.

Customers got bigger and calls also got bigger. Customers often brought along their Technical Architect or Engineering Director or Security Engineer to ask technical questions. We had Kevin. He was an ace at answering questions and we reached his capacity pretty quickly, so we added two more terrific Solution Engineers: Britt Jamison and Karishma Kothari. But we still needed more to match our customers.

To help with successful adoption of Slack and expansion of use, a whole domain of expertise existed called Customer Success. We had been helping customers as Account Managers. Now we needed to level up. Rav Dhaliwal joined from London and taught us what Customer Success meant, supporting customers with things like rollout plans and quarterly business reviews. Hot damn, those acted as catnip to hesitant fence sitters and skeptics, even before they had them. Just the promise of them painted a vivid picture of what success could look like for a customer. Helping them imagine that future turned out to be something they wanted very much.

Sales Math

So we improved how we matched customers in explicit and process-oriented ways that they needed. Solution Engineers handled the technical implementation bits. Customer Success managed the organizational change. An Account Manager quarterbacked it all.

But then we started to see that we had also started matching customers’ implicit needs with something I started to call Sales Math. Everyone expected that each side on a call would have roughly the same number of contributors. Each contributor would have a role on the call, like in the cast of a play. Each contributor would have a kind of counterpart on the call.

If this symmetry didn’t exist, if the contributors to a call didn’t balance the Sales Math, the call more often than not, didn’t go well. We at Slack would get hit with questions or issues that needed to call on expertise not present. We hadn’t prepared well enough. The customer would need to wrangle their internal people to move things ahead. They weren’t ready to proceed.

Was that always true? Not always, no. But we almost always needed an equal number of people on the call as the customer. Sales Math showed that each side was dedicating equal resources to the call. Specific people could be prepared to tackle specific topics, whether they were contentious or just required some expertise.

When it went well, Sales Math meant if you were an Account Manager leading a call, you could sell your organizational strength and show the customer how important they were, how many people were dedicated to their business. You could also push some topics to specific people in a way that felt transparent. Get a tough question? Repeat it and ask one of your own people on the call if they have any idea. Punt it to follow up on as an action item. Let someone else be the person to say no nicely. Circle back on it later.

So yeah, Sales Math showed us how we had to mature our processes and team to match our customers’ expectations.

Becoming Sales at the Offsite

We landed in San Francisco from the overnight flight, ready to get cracking. A mini bus took us north to Sonoma with a full agenda and big ambitions. The fragrant air and warm temperatures and golden light felt lovely landing straight in from Dublin in damp December.

Four of us arrived — the full Slack EMEA team — to join the 15 or so folks from Slack SF and Vancouver. The last thing AJ and I had committed to in our preparation calls was simple and hard at once: be brave.

AJ and I led our first session setting up the offsite — what we wanted to accomplish and how we wanted to engage. Our agenda looked ambitious and a bit daunting, so first things first, let’s be brave: were we Accounts or Sales?

I remember everyone expected this to be a contentious discussion, fraught with hard questions and conflicting views on our purpose. But then it wasn’t. We all agreed in 5 minutes. The thing we were doing was selling so we let’s be Sales. Okay, done. Great! Decision made.

It felt like a weighted lifted, like we as the leaders had expected we’d have to really sell Sales to the group. We expected to swim into the current and the tide had flipped. We were Sales.

The rest of the agenda proceed well. The team photo above captures pretty well the feeling of that day. We were together. We knew who we were. It was time to go and show the world.

Up next — Meet the new, new, new boss: Feeling our teenage years. Finding a top-1 leader for growing Slack. Hiring our new boss.