Lessons from Stripe

2019-03

I worked at Stripe for 3+ years, mostly as an engineering manager. The experience taught me a lot. In a few respects though Stripe totally changed my outlook. Here I’ll share what I learned in those areas: optimism, ambition, and recruiting.

Optimism

Stripe is for optimists. From their values:

We believe that Stripe will be far better in the future than it is today. When considering ideas, we think “how might it work?” is more interesting than “why will it fail?”

That sounds reasonable, but is hard to do in practice. When you’re trying to transform the global payments system with a staff of 200 people, a) things are constantly on fire and b) there are lots of good reasons to believe you’ll fail. Stripe’s optimism meant not letting those negative thoughts drag down the team.

We wanted to be optimistic because it’s mostly a self-fulling prophecy:

And we think that ambitious, energetic, and deliberate efforts directed towards progress are surprisingly effective in improving the state of the world around us.

Perhaps even more important (and unstated in Stripe’s public page) is the effect of optimism on the work environment. It’s draining to hear constant pessimism. In contrast, positive energy from your teammates is encouraging and contagious.

Optimism was the emotional equivalent of free money. It was thus highly beneficial for Stripe to adopt this as a top-level value.

Against my natural pessimistic instincts, I’m now intentionally optimistic in my work.

Ambition

All startups say they’re ambitious. You better be if you take venture funding!

Stripe’s insight was that tackling ambitious problems doesn’t just make the potential prize bigger. Ambitious efforts are often more feasible than smaller ones, because the strongest people want to work on the most ambitious efforts. In our experience this positive talent effect was stronger than the negative effect of problem difficulty. So, paradoxically, tackling a bigger problem could be both more rewarding for the company and in a sense more tractable.

This probably needs to be qualified. Stripe is set up so that we’re successful when our customers are successful (in real, economic terms). Ambitious problems for Stripe look like enabling more internet businesses and supporting entrepreneurs in more countries, not getting more ad clicks. The talent effect of ambition certainly applies to Stripe-style problems, but I’m not sure if it’d work for something like ads.

Based on my Stripe experience, I now advocate for almost unrealistically ambitious efforts (and only work in domains where this gives a positive talent effect).

Recruiting

Stripe was, correctly, renowned for the strength of its team. That was a function of the founders to start. Over time it also required excellent recruiting.

Again all startups say “our team is our most important asset”; leaders say “the hardest part of my job is hiring good people”. But what most companies actually do day-to-day on recruiting is disastrous: generic job ads, clueless outside recruiters, screening on brand name, candidate-hostile interview processes, slow response times, etc. The poor recruiting results of most companies reflect the work they put in.

Stripe was different in two respects: effort and thoughtfulness.

In terms of effort, Stripe’s recruiting was absolutely relentless. On the front of the pipeline this meant investing in potential candidates that wouldn’t apply for years, through genuine 1:1 relationships as well as many small events that introduce Stripe and its team. Once candidates were active, Stripe tried to move very quickly. Ideally we'd turn around recruiting steps on the same day: respond to the candidates inbound email the same day, and even decide on and give them an offer on the same day as their interviews. We could close candidates before Google replied to their initial emails.

Stripe was also thoughtful in recruiting processes. This signaled to candidates that the company was clueful and understood the candidate’s perspective. One example is Stripe’s capture the flag program, which not only put Stripe on the radar of a lot of candidates, but also gave them a sense of the strength of the engineering team. Another example was Stripe’s guidance on what to expect for interviews. We’d send candidates a PDF describing exactly how their interviews would be conducted, how they’d be evaluated, and how to prepare. These certainly helped candidates present their best work in the interviews. But they also showed that Stripe actually cares about this, which candidates knew from experience many other companies did not.

There's way more to Stripe's recruiting practice than I could describe here, but the meta-lesson for me was that it’s possible to be way better at recruiting than the standard Silicon Valley company, and thereby build a great team.

Working at Stripe

Stripe was a special place to work and I recommend it. If you’d like to talk candidly about what it’s like to work there, or to be introduced to hiring managers, I’m happy to chat.