[wanderr]

Ex-Dropbox manager here. I also built BetterHelp (sorry) and I was the VP of Engineering Grooveshark.

Dropbox was the first job I've had where managers are not expected to code although they still go through a small ramp up where they can fix a tiny bug or make a hello world commit and deploy it to production to show that they understand how some of the systems work. Due to some crazy circumstances with the team I took over, I never even got to go through the ramp up. I was thrown straight into the deep end leading a team dealing with an urgent crisis that could end the business.

It was scary as hell, going from what in hindsight had been a "TLM with extra responsibilities" in my previous jobs to a full fledged EM role with all of the same accountability for quality and timely production, but none of the direct control. But I quickly realized that I was surrounded by people who were at least as capable as I was and usually more brilliant.

I think my greatest technical strength was always in eliminating technical complexity, making systems more robust and maintainable. It turns out you can still spot the blinking red lights of unnecessary complexity just by talking about the systems from a high level and asking the right questions, and when you help other talented engineers see those problems, they will naturally want to fix them. No need to jump in and do it yourself.

Once I knew I had a team I could trust and understood the strengths of the different players, I had to shift my focus to learning how to be a real manager. Managing people is a wildly different skillset than writing good code or building a good product, and I realized that I had never really been a manager despite leading teams of people. My apologies to everyone who ever worked for me before this point. Without realizing it, I had always treated the human factor as an annoyance and I probably hindered the growth of past teams a lot by stepping in and doing the high stakes, high urgency stuff myself.

When folks grew under me, especially at Grooveshark when I was young and immature, it was a happy accident and not something I was very intentional about. At Dropbox I really learned the importance of investing in people, giving them opportunities to grow and creating space to allow them to make mistakes. I didn't touch a line of Dropbox code or ever commit a thing, but my teams were high impact and many of the engineers who worked with me told me I was the best manager they've had.

Now I'm a co-founder at my own startup and, of course, I'm writing code again. Yeah, I'm a little rusty with some of the language specifics but I've been talking to brilliant engineers about their work for the last 7 years, when it comes to robust system design I'm probably a better engineer than I was the last time I wrote production code that was used by tens of millions of users. I will of course be in the hybrid role of building and managing folks for a while, but I hope I can keep my manager chops honed and support my team properly as I build and grow it and, eventually, stop writing production code again.