Last week was officially my final week with Trustwork, a seed-stage startup where I joined about two years ago as the second engineer. It’s an equitable conclusion to a personal journey that began when I decided to leave three months ago. I’ll be joining the Issuing team at Stripe in a month, a relatively new team with a really audacious charter.
In the lead-up to making my decision to leave, a couple of factors came together to bring my shields down.
This is a difficult question to answer publicly. Many of my reasons stemmed from a self-assessment of my career up to that point and where I wanted to go, and how that fit with what the company was doing. These are some of the factors that I might have considered, presented as a series of rhetorical questions so as to avoid potentially disparaging discourse:
Occasionally, I take some personal time to decide if I’m living in a way that gets me closer to the person I want to be and the things I want to accomplish. This past March, I was grappling with a bunch of questions of the form “How can I achieve x at this company?”, where the set of x‘s are personal milestones that seem directionally appropriate for the next few years of my life. Can I make these questions easier to answer if I dropped the “at this company” constraint?
One particularly important personal life metric is my rate of growth in skills, knowledge, and decision-making capability, and my blind spots in particular — what am I not good at that I don’t even recognize as a skill? Am I really doing a good job and making a difference that will matter beyond the end of the current sprint? Do I have a sufficient quantity of, and clear enough, feedback loops to update mental models and reliably learn?
People often talk about startups being an incredible journey. Platitude aside, the journey tends to involve a lot of stuff that didn’t work along a winding path that, with luck, leads to eventual success. How much is learnable from each failure and from each success? How much meaningful signal is there among all the noisy data points? This isn’t as straightforward as it might seem. It’s possible to learn a lot from success — to analyze the inputs that went into making things work, why those decisions were made, and so on. It’s also possible to learn little from success, such as the case where everyone celebrates and moves on. Similarly, it’s also possible to learn a lot from failure, or to learn little from failure, such as the case where failure is swept under the rug and never discussed. In a company, this is likely determined by cultural standards around decision analysis and degree of intellectual honesty.
One additional consideration I had in mind was whether I continued to believe in the value of the equity I had. Working as an employee represents an all-in investment of time. Given the information I have about how things are going and the amount of control or influence I have over future decisions, is the expected value worth it?
How Was Interviewing?
After I decided to leave, I procrastinated a lot before actually doing anything about it. It felt like making the decision to leave was hard mental work, and I wanted to give myself a break — but of course I hadn’t actually done anything yet. In my case, it was three weeks before I started planning out my timeline and topics to study. I’ve talked to people who’ve waited many months between deciding to leave and actually starting to do so.
Coordinating timelines between multiple companies was surprisingly difficult. From the beginning, I wanted to schedule every step so that all my onsites would happen in quick succession (rather than spread out over several weeks). I didn’t let myself think about what it would actually be like to receive offers (in the beginning, I had no expectations of making it anywhere), but in case I did, I also wanted to make sure they would arrive at the same time so I could negotiate them. For each company I talked to, I determined the steps in their process and how long it would be between each by asking friends at each company if I had any, or during my first call with each recruiter if I didn’t. Early on, I stressed a lot about trying to schedule calls so I wouldn’t end up too far ahead or behind with any particular company. Looking back, it helped to set a deadline for myself and establish this timeline with every company I spoke to. In my case, I told everyone that I would be making my decision by the first week of July, and maintained that timeline throughout the process with each company. For the ones that were moving slower, I was able to use this consistent timeline to drive some urgency, which helped me keep things moving mostly in lockstep. My onsites ended up on nearly-consecutive days, and — by a stroke of luck — I received three of my four eventual offers via consecutive phone calls one particular morning.
I studied for about five weeks before starting to officially interview, and continued studying right up until my last interview. Interview prep can be an interminable game: there’s always more to learn and more implementation details to unforget; there’s always a feeling of “I could prep more”. But at some point, you actually have to go for it.
I didn’t actually expect to get anywhere with Stripe — without any connections to refer me, I sent in a cold application from their website and figured that it was unlikely I’d hear back. But a few days later, I did, and proceeded through a concise series of calls and interviews. I was impressed throughout by how nice the candidate experience was, from the structure of each interview, to the people I met in each, and how quickly feedback was returned after each round.
After my first call with my recruiter, he switched me to a team I hadn’t considered, but has turned out to be incredibly exciting. The Issuing team is still small, which means I’ll be able to work as a generalist, understanding all aspects of the product, rather than working within a specialized box. I genuinely enjoyed all of my (many) conversations with people at Stripe, and of all the companies I interviewed with, Stripe’s culture resonated best with me.