Leaving Stitch Fix

September 03, 2019

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I’m no longer working for Stitch Fix (this was 100% my choice to be clear :). It’s been an amazing six years, so this post is a hopefully short one about why, and the next post will detail what I’m looking for at the moment.

Why leave?

I joined Stitch Fix in Feb 2013 as the third engineer. In that time, the team grew to over 200 people, the company grew to become a public, profitable, intentional business, and I learned a ton about a lot of things. I certainly got more than six years’ experience out my time there.

I also was fortunate enough to grow with the company. I started as a lead engineer, writing code. I eventually became a manager of a team, then a director managing multiple teams, before settling into a chief architect and technical project management role. I had my hands in a lot of stuff over the years, and I got to do this entirely remote from my home in Washington, DC. While I did travel to HQ in San Francisco frequently, I thankfully never had to move there.

The company continues to be well run by really good people. Any time I’d interview someone working at another Silicon Valley “BigCo”, I was immediately reminded just how good the culture at Stitch Fix is. Despite that, it’s no longer the right place for me.

I thought it was my duty to continue growing with the company and to continue to operate as a senior leader at what was no longer a startup but was now a large (at least to me), going concern. But this is not my duty and there is a huge difference between building a company and team and operating a company/team. The former is what I like and am best at.

So, rather than get sullen, angry and jaded while making a half-assed attempt to find another job, I decided to take some time off to recharge and figure out what’s next (and I realize this is not something most are able to do and am thankful for the stars having aligned so I have the privilege to do so).

In my mind, this is the right way to leave a job - on my terms, without burning bridges, and leaving the company better off than I found it. My role will get filled by other, more interested people. They can amplify my good decisions and correct my mistakes.

What did I learn?

A lot! The next post outlines some of the more specific experience I gained, and this blog will certainly be littered with posts about particular insights. I will say that, broadly, you don’t have to do things the way someone has prescribed or the way “everyone else” does it. Stitch Fix IPO’ed with no product management org, one front-end developer, and a three-person ops team—the rest of the 99-strong engineer team were generalists. That is not the Silicon Valley playbook!

What’s next?

As I mentioned, I’m taking time off before whatever is next. I am open to part-time consulting work in the interim, because what I want to do is meet a lot of people working on interesting problem and see if the somewhat unique experience I’ve had can be helpful to others. The next post on my blog talks about that in more detail.

In the meantime, I’m hoping to do more writing, more Holga photography, and more diving. I also want to spend some time studiying areas of software development that are too difficult to do while working (the event sourcing in the small post is an example).