Please sit next to the money

Slack starts to take off. Is that with or without me? The polite struggle for control. I get hired, fired, not hired, then — what? “Please sit next to the money,” says my wife.

My first consulting contract for Slack was with Tinyspeck Consulting Services. I started on June 5, 2013, as the ninth member of the team, and third member of the team in Vancouver. Five team members were in San Francisco. One other team member was in New York. We were small.

My consulting contract ran for 3 months, until September 5. As we approached the end of August, I asked Stewart what he wanted to do once the contract ran out. He was into businessman things and working on a ton of other tasks at the time, so I let it slide when an answer wasn’t forthcoming.

I felt good about the work I’d done and the results we’d achieved. Our preview release on August 14 had been a very big success — certainly much larger than we’d anticipated or expected. There was a significant buzz from people who had tried the product or wanted to try the product. The team felt like it was operating at a high level and I felt like I was contributing.

Ideas for Slack PR during our Preview Release, Nov, 2013. We did so few and so many of these kept coming up as good ideas in the years that followed.

In addition to marketing, the daily work I was doing I thought of broadly as "helping and talking with customers.” It was part marketing, part sales and even part support. I ended up doing pretty much anything that needed to be done to help a customer understand Slack and start using it successfully, including inviting them in the first place.

The days were really busy and I remember after every one of them going home to say, “there’s just not enough time to get everything done that needs to get done.” It felt hard and exhilarating at the same time.

Slack takes off

One of the jobs I picked up was combing through the continuing stream of inbound requests to get an invitation to try the product. We had hooked all of the requests for invitations to a Slack channel I monitored.

If I spotted a request that looked interesting, which basically meant an interesting name or email address, I dug in and did a little research. It seemed to me the simplest thing to do — follow up on some bit of curiosity to learn more. These were folks who were interested in Slack and had heard about us, we might as well know something about them to maybe make their experience better.

I singled out any that I thought deserved special attention. Were they a name brand I knew? Did they have some technical or publicity status? Could they be connected somehow? Did I recognize their name?

If I felt like the request could be higher value, I would prioritize sending them an invitation and give them white glove service for onboarding. I did demos. I answered emails. I set up calls. I wrote help documentation. I linked to help documentation my teammates had created. I helped people see the difference between what they were using for communication and Slack.

At the same time there was other work to do. The press attention had quieted somewhat but still burst into life on occasion. Folks who had received an invitation started to write about their experience on places like Twitter and their own websites. Almost universally these were positive, but occasionally they needed a little attention or response. The feedback grew so that I started to categorize it and then report it back to the team.

All of this work felt essential and valuable to me. No one else was doing it except Stewart. I was nearing the end of my contract — did he want to continue?

Yes, he told me one day almost as an aside as we walked for an afternoon coffee. “Let’s do another month.” So I wasn’t fired and I wasn’t hired. I was just ongoing.

The same thing happened at the end of September for October, and at the end of October for November. The work kept increasing in volume. More people signed up. More people joined the Slack instances of those who had already received an invitation to try the product.

At the same time, we were still working through the backlog of folks who had requested an invitation in the first place, from the very first announcement of the preview release in August.

I remember one day Stewart asked me how many invitations we’d sent out that week. The answer was a relatively small number — in the hundreds. I’d estimate we had over 10,000 to get through by that point, but our process had been careful and high touch. We wanted to give people white-glove service. We talked about customer experiences we aspired to — the Four Seasons Hotels, great restaurants where everything was in sync.

When I told Stewart we’d only sent out a few hundred he was mad. I don’t have any other way to characterize his response. Maybe exasperated? This was not what he wanted. We needed to send out more. We needed to get through the list. A new urgency arose in that conversation. Why had we been waiting? It struck me that he’d had conversations and those conversations had escalated his sense of urgency. But this was new to me. Okay, I thought, let’s go.

So we changed tactics and started to blast out hundreds of invites every few days. Responses started flooding in and we needed to shift from our individual inboxes to a group support tool where many of us could answer inquiries and we could pass off complex inquiries between us. If we thought it was busy before, now we had a taste that the demands were only getting started.

Escalate the medium

Through it all, we sought to assume our customers were smart and had good intentions. We received some angry responses and had to reply to them politely and constructively.

My wife had said to me wisely one day that when faced with conflict, better to escalate the medium not the message. So that’s what I tried to do. In any case where I felt I wasn’t able to connect with a customer or solve their issue in writing, I offered them a phone or video call. My calendar filled with these calls and I started booking them 1 week away, then 2 weeks away.

We approached the end of November and I wondered what would happen to me at this company. Was I ever going to get hired?

I felt like I was doing good work, but I also kept my distance. I had boundaries. I made a point of not working in the evenings, not working on weekends, and trying to keep work in its box. I also had other companies trying to hire me and I sometimes met with them to hear what they had to say. Was I really looking? No. But it didn’t make sense to only have a single option.

At the same time, the workload at Slack continued increasing. We had hired a few folks back in support and engineering so the team now numbered around 14. These folks were rehired from the Glitch team and were very good teammates. But they didn’t do the things that I was responsible for doing and that work showed no sign of going away, so something had to give.

I’d like to say we got more efficient or delegated or did something clever to meet the waves of customers we were lucky enough to have. But that would be untrue. The reality was we just worked harder and longer to meet the demands.

Tim (R) and Brad (L), collectively known at TimBr, were hired back to work on and run Slack integrations. With no meeting rooms, they used the hallway.

I started working in the evenings at home once my son went to bed. I started working a few hours on the weekends to catch up on high-concentration tasks that required sustained attention without interruption. This didn’t feel particularly healthy from a balance perspective, and it didn’t feel particularly good from a marital happiness perspective, but it seemed like it would be for only a limited time.

And, to be fully honest, I really enjoyed the work. My teammates were excellent. Customers really liked the product. It was all pretty joyful, as far as typing at a computer and talking on a phone or computer goes. It was also the best kind of hard fun. And it was nice to feel like I’d found a niche where I could be effective and contribute to our progress.

So I wasn’t altogether surprised when Stewart said in late November, “We’ll make you an employee.” It felt right, like I’d earned it and like the natural progression of things.

Then a few days later he said, “I know I said we’d make you an employee. But now I can’t.”

Oh.

He tried to explain. He asked me if I played music. I did not. He said that we were just not in sync. Working with me was like when you play music with someone and you can see they can play but you can’t get into a rhythm. Did I know what he meant? I did and did not. I could see he was struggling to explain things. And really, in the moment, did I give a fuck about his explanation?

He offered to write me a strong recommendation on LinkedIn. I’d done very good work and he wanted to make sure I was acknowledged for my work. Better yet, I could write the recommendation to say what I wanted and he could post it.

I remember the feeling of that moment well. It’s one of the few times in my life I have ever seen dark spots cloud my eyes. My heart raced and I felt faint. A cold sweat came on. Here was the startup dream I’d had chased for so many years, the company taking flight right in front of me. I thought I’d earned a place and would be included, yet it was being snatched away.

I told him I didn’t feel so well and needed some fresh air. Maybe to go for a walk. He thought that would be a good idea. The tension in the conversation lingered and started to dissipate. I went back to my desk and sat to gather myself. I breathed. He went back to his computer to pick up another task. Soon he left the office on a call. He physically moved on, out of the office. Businessman things. I waited a few minutes and felt better, less jittery and jangled. I left the office for that fresh air.

I walked to a nearby park full of squealing kids on swings and hovering parents on phones. I found a quieter bench and turned my face to the warmth of the sun. I called my wife and told her about the conversation.

Even years later, she has a very strong recollection of the details of that conversation. Much stronger than my own. To help with the story here, I asked her to share some of those recollections.

First off, working during off hours was not new to me or James. We had both worked for startups or had run our own businesses. And the great fallacy is that you work when it makes sense and that means you have more flexibility during the week. You could tell yourself, "sure, I had to work Monday night, but I took Wednesday morning off." In theory, this balances out.

In practice, it means that you have little separation between work and home. So here we were again, working evenings and weekends. But this time we had a six-month-old baby. For those of you without children or who were so sleep depraved that you've forgotten, babies are awake in two hour slots and then nap 30 to 60 minutes between. It's like having a day of back to back meetings. Each meeting adding to your to do list and then having zero time to actually do anything. And to add to the fun, I was still working. I was running Boxcar Marketing and teaching at SFU (Simon Fraser University). So not being able to trade off that baby was ... less good.

I remember the highs and lows of James's first conversation with Stewart regarding the job offer. This was a role that was really making James happy. His brain was sparking with ideas. He liked the team. It seemed like a success in the making. Stewart had a good track record. There were lots of rationalizations to counter any idea of accepting another job offer.

So Stewart's retraction of the offer, as I recall, had something to do with the board. And yes, it didn't feel good. It put a lot of pressure on us. James did not want to be a new dad without a job. But the position on offer with another company did not spark joy. His gut instinct was to stick it out with Slack. There was something about it that couldn't be expressed rationally. So there are times when you don't fight intuition. And this was one of those moments.

I recall telling James that if he wanted to be there, then he should just keep showing up and doing the work. As long as he was being paid, there was a job and an opportunity there.

After our chat, I knew that we would be okay. We’d been through rough things before and survived and we’d get through this. I still had the consulting contract to fulfill. I had others who wanted to hire me. I had options that could also be good. As good? Not likely. But I told myself I didn’t know. They could be. Feeling reset, I went back to work. I had to get my laptop after all.

The polite struggle for control

The next day I showed up again. I clarified what Stewart wanted — me to wrap up my work for the end of the month or to do another month of consulting? He wanted another month of consulting, wrapping up at the end of the calendar year. Okay, once more, let’s go.

I did the work I thought needed to get done in a bit of a blur. I went home. I repeated that process for a few more days, trying to put the uncertain big picture out of my mind and focus on the next task I had to do right in front of my nose. I started to let go of some of the tasks I had taken on because they weren’t going to be mine soon enough.

I’d like to say that my focus on the next task in front of my nose was an effective tactic to deal with my disappointment and frustration. Sometimes it was and I could get lost in the work. But sometimes it wasn’t and I felt distracted. I gave myself a few pep talks to keep going. You put your name on every job you do.

Then in the early days of December, something changed. I was still working on the tasks I had taken on and that work was increasing in volume and intensity. I was also working more tightly with the rest of the team, picking up customer inquiries from the support team, sending along product feedback to the engineers, coordinating PR with an external agency.

It felt like, to use Stewart’s analogy, I actually was in a rhythm with folks. When we had an outage and the product went down, it was all hands on deck to handle inquiries, and I was there, metaphorically shoulder-to-shoulder with the whole team, dealing with customers as if I was part of the business.

The other thing that happened in those early days of December is I gave up — I gave up thinking I had control over anything at Slack. I gave up struggling with Stewart for control over work. If he wanted to be the boss, and he did, that was the exact word he used for his role with the company, then I could deal with that.

In all my consulting life beforehand I’d always considered each engagements as a polite struggle for control over the work. The client thought they knew best, and they often did, but they had also hired me for my expertise. So I had to manage the process and deliver on that expertise. I was responsible for the work. I should have a goodly amount of control over it. After all, as the classic analogy goes, why get a dog and then bark yourself?

But with Stewart at that time I had to change my approach. I don’t know whether I recognized this consciously and made it an explicit decision. I didn’t go for a walk and consider options for how to get in rhythm. I just needed to try something different. So I gave up any sense of control and focused on just executing my work as well as I could. That’s the change that happened in December, 2013 for me.

So what happened behind the scenes? I don’t know. But for my own sense of having a clue about the world, I can make a guess at a few things that could have influenced things and helped get me in rhythm with the team.

First, I had started to work with more of our larger customers, doing demos, helping them with the product, creating and then giving them materials to help with their adoption. When materials weren’t available, I created them. When questions were new and we hadn’t answered them before, I figured out how to answer them.

I used simple sales practices: research the customer, ask good and open questions, listen to their answers, fit the conversation to what they needed, reflect their priorities, set next steps, follow up on time and with details, build their trust in the product and process as a guide to helping them succeed.

It wasn’t rocket surgery to do but it did require a certain compassionate and bovine temperament that I was lucky enough to possess, mixed with a bit of technical know-how and some tenacity for pushing things ahead. I think these customers felt like I was someone they could get in touch with easily and who could reliably help them.

So this was going very well. It was certainly immensely helpful that we had a kick ass product that people loved. I think that some of those customers I was working with ended up knowing Stewart, or knew other people he knew. In any case, word got back to him through connections and beyond that working with Slack was easy and a pleasure, and by transference, I must be doing a good job.

Second, working with the rest of the team at Slack was going really well. With the increase in customers, confidence had increased and we’d hired a few folks back from the Glitch team in support roles. Ben Jenkins lived outside Detroit and thrived working with customers. Carrie Stevens was quick on the draw and generous with her expertise. MacKenzie Allyn was a wizard behind the scenes triaging inquiries. They were all excellent to work with and it was fun work to do, and if Stewart had asked my teammates about working with me, I think they would have been positive references. We had developed a rhythm.

Third, I think there could have been a weighing of alternatives. Would Slack hire someone else? Would someone already on the team do the work I was doing? Could the work I was doing go away? How quickly would an alternative be to find? I’d guess that none of those options seemed as simple or as easy or as fast as just pushing ahead. Stewart didn’t at the time have a strong background in business-to-business software sales or a network of people he trusted in that business. I think when he considered replacing me he found that the best option was just to have me continue to do the job.

Fourth, I had been around Stewart long enough to have developed what I thought of as my own version of his voice. On demos and customer calls, I had started with his voice and phrases, keeping those that worked and substituting in others of my own when they didn’t. In writing, I had adopted some of his mannerisms and evolved them into my own. As an undergraduate arts student I had studied film and there was an element of ‘method acting’ required that I’d gotten better at over time and then had evolved into my own approach. I did a very solid Stewart.

Last, I think Stewart foresaw that we wouldn’t work together in the future as much as we’d worked together in the past. The work I was doing and that needed to be done was much more independent. So did we need to be in sync? We were adding customers all the time and would continue to do so. My work seemed to be working out with those customers and with teammates, so why change it? Was it a top priority to work on for him? Maybe. Maybe not. I don’t know.

In any case, despite Stewart’s sense that we weren’t in sync, I’d found a sweet spot in the company where I had valuable work to do with very good people I enjoyed working with.

Please sit next to the money

On Thursday, December 19, 2013, lives a calendar meeting with Stewart that I can still see because it was sent to my personal calendar.

Title: Coffee talk. Location: The Future!

Earlier that week he’d sent me a message saying he wanted to revisit making me an employee.

We met once more where we had first met: JJ Bean. Stewart had a small, bullet-shaped aluminum coffee cup he used for his triple macchiato. We left the shop and went for a walk around the seawall of Vancouver, a public pedestrian and cycling path that borders the ocean to wrap most of the downtown of the city. Like many of our conversations, the meat of this one only took a few minutes. But we talked for more like 20 minutes as we walked.

Fall walking on Vancouver seawall.

That thing I was doing working with customers? Doing demos? Helping them with the product? He wanted that to be my full job. We’d call it Accounts or Account Management. Did I want to be the Senior Manager of Accounts? I felt excited and apprehensive. Yes, I wanted to join the team. Did I want to do it in a Sales role?

He went on with his rationale. Marketing would need to live in SF longer term. We never talked about me moving to SF but I don’t think that was ever a real option. In truth, I think there were most likely many more people with much more talent for business-to-business software marketing in SF than me. This was the start of a taste of the buying power Slack was starting to have for talent.

I gave him an initially positive reaction and said I’d need a few hours to talk with my wife so we could make a decision together. Stewart and I walked back to the office together, I think both somewhat pleased with how smoothly the conversation had gone.

I called my wife and shared the conversation with her. I liked the company and the work and everything, except I was concerned about moving to Sales. My wife, once more the clear brains of the operation here, said she’d seen lots of startups and the first thing that always gets cut in any rough times is marketing. Get into Sales. No one will ever wonder if you’re worth keeping. You can show exactly how valuable you are.

Her exact words: “Please sit next to the money.”

And she was right. Here’s her recollection of that time.

That second meeting with Stewart was more memorable to me. As I recall, it was pitched as a sales role and James balked at that. He didn't want to do sales. WTF was my reaction. But at the time, sales roles in tech companies were a little smarmy. There was a divide between marketing and sales. Literally. These teams often sat in different parts of the office, accessed different resources, and had a bit of disdain for each other, peppered with some resigned respect depending on how leads were handled. I got that. But everything James had told me about Slack screamed collaboration. After laying out my thoughts on his reaction and pressuring him to drop his perceptions of what a sales role involved, the compromise he came to was that if the role could be called Accounts or Accounts Management, then it was more palatable. And I definitely said, "please sit next to the money."

So, Accounts it was. I accepted the offer with one request: a change in title to Director, Accounts. Start date was immediately after the holidays, January, 2014.

My second job at Slack was about to start.

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