Figuring out whatʼs next

At the end of the first week of 2022, I left my job at GitHub after six and-a-half years. It was a hard choice mostly because I wasn’t unhappy there, I had just done some of the best work of my career, I had built a network of people that I trusted, and I had an incredible sense of job security. So why did I leave?

A few months before I decided that It Was Time™, I had a discussion with someone that I trust implicitly with my career. During our talk, it was pointed out to me that unknowingly I was exhibiting signs of someone who was looking for a my next thing. The GitHub that I joined in 2015 was a very different place than it is today. You could change just about anything with a pull request (and were encouraged to), even though management had just been implemented, much of an employee’s expectations were still tied to shipping / output. This meant that as a product designer you got to wear a lot of hats, processes were loose and experimental — if there at all, and you really got a sense that everyone at the company was all pushing toward something together.

As GitHub grew and scaled, more formal processes were built around the work we did, things became more complicated as more specialized roles were added, and the path to shipping the product grew longer and less straightforward. The entrepreneurial instincts that I had in my first few years were slowly exchanged for figuring out how to fit in bits that I cared most about into the larger product.

Working as an IC for a big tech company in 2022 provides a lot of niceties: you get consistency, job security, above-market salary and equity compensation, and if you’re there long enough you get to specialize in things. The tradeoffs are your own personal impact on a company / directional level, the ability to take big risks, and straying outside of established processes without asking for permission/forgiveness. Depending on what you’re seeking out of work, you may land on either side of these tradeoffs: predictability, compensation, and job security vs. autonomy, individual impact, and the ability to make big bets. The more I talked and thought about it, the more I longed to exchange one for the other.

A framework my next job

At a certain point after this conversation, I realized that I never wrote down the things that I wanted from a potential employer before. I had a lot of ideas about the type of role that I wanted, but not the type of place I wanted to work. Back in 2020, after a few years in a management role, I realized that it wasn’t for me so I dove head-first into a staff designer position. There’s been a lot written about the pursuing a senior+ IC designer track, but I’ve never thought about evaluating this at a company level before. Also around this time I stumbled upon Muan’s On looking for a job, which I would recommend to anyone in tech looking for their next thing. With all of this rattling around in my head, I decided that I needed to formalize some type of framework to help me decide what’s next.

1. Type of product / design

   Working at GitHub made me fall in love with designing developer tools. I get a lot of joy out of making tools for people who make. In my next role, I knew I wanted to stay in this space and perhaps get even more focused on a singular aspect of it. It is developer tools or bust for me. Product taste is also played a role in this, even if the money was good, I couldn’t pursue any company whose products I wouldn’t use myself and truly believe in.

2. Stage and size of company

   This was a big one, perhaps the biggest one and the reason why I started to get itchy at GitHub. Later stage established companies have a lot to offer (see above). At this point though, I really wanted to get in somewhere as an early employee. I wanted to shape the design culture, figure out our own processes as we go, and be a high leverage IC that has a hand in everything. In my case it was a matter of figuring out what I didn’t that helped me navigate this. For example, even getting in at a hyper-growth company with a couple hundred people felt like I would be repeating the last five years of my time at GitHub again (scaling from 300-3000+). I knew I needed to find something that was even earlier: 20-30 employees, series A/B round, and with obvious growth potential.

3. Equity / Salary compensation

   When considering a move from a big tech company ➡️ startup, getting paid usually also means taking on more risk. Typically early stage companies offer less cash salary than and more potential for equity growth. My financial situation allowed me to take a bit of a salary decrease, in exchange for more upside on my equity. Startup equity is hardly a sure thing, but I wasn’t going to take a position at a company that I didn’t have confidence in.

4. Management structure

   Another hard requirement that I had was that I had to, for now, report directly to a founder. This was a forcing function for me not to step into a company that was top-heavy with management, too large, or too process heavy. I fully expected that this wouldn’t be a forever thing, but a near-term thing that would allow me to help scale the design org and eventually hire my own boss.

5. Tech stack / tooling

   There’s a quote from Picasso, “When art critics get together they talk about content, style, trend and meaning. But when painters get together, they talk about where you can get the cheap turpentine.” (I’m sure this isn’t really what he said, but it sounds good!) I am very comfortable with certain stack of design tools and front-end development tech, and veering too far outside my comfort zone wouldn’t allow me to do my best work. Because I was looking for a position where I would be involved in front-end engineering, a modern tech stack was important, engineers who care about performance, design systems, and scalability were all must-haves.

6. Operations

   There is a really fuzzy line between too much operational process and not enough. It moves around as a company grows, and usually companies are on the either side of the line. While having a formal HR department wasn’t a hard requirement for me, formalized People Ops was. This could be a single person or an entire department, but I needed to know that there was some structure around things like raising concerns, asking questions about benefits or company policies, and a channel for career advancement.

   Additionally, I wanted to make sure that the company had a remote-first culture, in 2015 this was more rare than it is now, but any requirements to move or eventually go back to an in-person focused environment quickly disqualified a role for me.

My Goldilocks zone

After talking to multiple companies, I only really seriously considered one position that fit into to the criteria of the framework that I laid out. In the second week of January, I joined the team at WorkOS and I can’t wait to share what we’re building. The process taught me that patience and really honing in on the things you care about and letting go of the things you don’t is the way to find a job that leads to personal happiness.