What Stripe Gets Right

I recently made the decision to leave Stripe and join Macro Oceans full time. This was a difficult decision and was more about not wanting to miss the opportunity to build Macro Oceans rather than quitting Stripe.

While I was working at YouTube, I began doing something that really helped me: team and company cultures the way I would about a friend. They have a lot of good qualities and some faults. [0]

But when you’re working somewhere everyday, even little faults can be really grating, the way that you might have a friend you really enjoy who you can’t stand after two weeks traveling together.

Part of my breakthrough was to spend more time focusing on the virtues rather than the faults. I also began to accept that the faults developed over time and would take time to change. This made it easier for me to navigate through the things that drove me a little crazy: it was part of what made the place what it was.

With this context, I want to reflect a little bit about what Stripe gets right, if only so I can remember it. These aren’t the only things about Stripe or a balanced picture of what it’s like to work there, but the things I want to remember and to emulate. [1]

• Ambition: Stripe is a place where you are asked to do work that changes the world. Even if you’re starting small, you’re looking towards the bigger picture and asking how you can do more, faster. This can be uncomfortable, but having worked places where this wasn’t a part of the DNA, I really appreciate it.
• Brand building: Stripe has mastered the art of elevating their work through story telling and myth making. This is truly cultural. I spent more effort polishing a demo for an all hands than I did for external communications at prior companies.
• Talent: Somewhat related to the brand building, the level of talent at Stripe is the highest of any place I’ve worked. [2] The conversations within my team happened at an incredibly high level, which is infectious. It’s fun to work somewhere where you are pushed to do your best work just to keep up with others. Somewhat related, I have so many people I’m going to miss working with.
• Engineering culture: The craftsmanship of the engineering teams in particular will always stick with me. Stripe is not a place where the user experience is pushed off onto Product Managers and Designers. This is modeled by senior leaders — engineers are expected to care about making something awesome. As a product manager, this makes my job so much easier. I still have to make the case for priority (should we solve this problem next) or return on investment (is this worth the time we’ll spend on it), but never for quality as a principle.
• Responsiveness: Individual Stripes react quickly to problems. You see this on Twitter where posts about problems lead directly to responses. Stripe as an organization reacts to changes, be they market conditions or other strategic factors. New information is put to use quickly.
• Ideas: Stripe is a very philosophical place. One of my favorite parts of working at Stripe is a slack channel that is devoted to strategy, but the art of doing great work, building a great company, and where progress comes from. Whenever I was in the midst of a particularly fast paced project or under a deadline, this slack channel kept the creative aspect of the work in my mind.

0: At every company where I’ve worked as an adult, with one possible exception, the good qualities outweighed the faults pretty significantly.

1: I enjoyed my time at Stripe and on some level wish it had been longer. If you’re considering a job at Stripe and want more detail about my experience, feel free to reach out: jdillaxyz@gmail.com.

2: The possible exception here is Bain. The difference that at Stripe the talent level is high and distributed across functions whereas Bain everyone basically did the same thing — corporate strategy.

2023-06-01