Almost six years at Slack

Five years, eight months, fourteen days. 35,000 simultaneously connected users when I started. More than 10 million when I departed. All with working lives simpler, more pleasant, and more productive than without Slack. That mission — to make people’s working lives simpler, more pleasant, and more productive — always felt noble to me in a modest, self-aware way.

I’m grateful. That’s the feeling that stands out from all the others. Stewart’s pithy advice to startup founders is to “be really lucky.” Check. I met Stewart and Cal when I was an intern at Yahoo! and pestered them just the right amount to make an impression and get a job at Flickr. Lucky me! They hired me again to lead Operations Engineering at Slack. Lucky me! At the time, I had no idea just how lucky. In hindsight: Very.

They trusted me to rise to a challenge larger than any of us knew. In every form, exponential growth is humbling. Carrying on like that for almost six years was exhausting and exhilarating. What can you do? Do the thing you think will make the biggest impact, welcome help from others, and repeat.

I created Slack’s compliance program when, on my first day, Cal greeted me by saying, “I’m so glad you’re here; we have a meeting with auditors today.” Over the next few years, before we had a Solutions Engineering team, I talked the ears off of dozens of customers, explaining Slack’s security posture and how anything and everything worked.

Officially, I began as Slack’s Director of Operations. Management. But I didn’t commit fully. Management’s a full-time job — and then some — and doesn’t tolerate folks who, like me, try to hold onto all their engineering responsibilities.

The results weren’t all bad. My focus on the technology served us well during a security breach in which I led my team to move Slack from EC2 Classic to VPC, replacing every piece of infrastructure that was ever compromised (and also every other piece of infrastructure, just for good measure), in three days, production first, with no practice. A security breach, by the way, is one of those experiences I wish every engineer to have had but do not wish anyone to have.

My tendency as a manager to put technology first did not serve us well the rest of the time. I was too in-the-weeds to see what my people needed and where we could make the biggest impact, too hamstrung by technical responsibilities to rally the help we needed to make the biggest, most impactful changes. After almost four years and after growing to almost 40 people, I recognized that management did not elicit my best work. So, I pulled the old switcheroo. I found a new Director to be my boss. I was an engineer again. A leader, not a manager. It was liberating.

What did I do with all the time I no longer needed to spend on performance feedback? Well, Slack was missing a highly sought-after feature that sat at the intersection of product, operations, security, and compliance. Who better than me to thread the needle? After standing at a whiteboard for quite some time and with the welcome help of engineers, product managers, designers, marketers, salespeople, and our friends at AWS, Slack EKM emerged.

It’s amusing to me to look back and remember that Slack was my first experience using AWS professionally. I went from enthusiast-level familiarity in 2014 to the AWS Customer Advisory Board in 2018, with a budget that could run a small town. I learned quickly and listened to the smarter people I’d hired. I set us up to survive, if not always thrive, through years of exponential growth. Every week for almost six years, the Slack of that week was the biggest website I’d ever worked on.

I feel accomplished. I also feel thousands of nagging doubts, regrets, and urges to do certain (mostly little) things differently. “Next time,” I think. That’s the positive way to think about all these little things. After all, these mistakes weren’t critical errors. They didn’t sink the ship. They were lessons to be catalogued and synthesized alongside all the others. They shape the future. Next time, if I’m lucky, I’ll make all new mistakes.