100 days at Stripe

A few thoughts on beginning a new job

I recently passed my first 100 days at Stripe in Product Strategy & Operations, working within the product org to spot opportunities, shape priorities and get things moving across teams. It's interesting how much the actions you take in your first weeks ripple out into the months that follow. Urgency is a value people genuinely live by here: there's a bias toward moving now rather than waiting for perfect conditions, and the pace you set early on tends to carry. Like a flywheel, once you have momentum each push goes further than the last.

"Once you set the pace, the rest will follow."

Haruki Murakami, What I Talk About When I Talk About Running

It's worthwhile taking the time to understand your role, your team and the company in more detail. When you join a place like Stripe, there's a lot of context below the surface that isn't obvious on day one. Much of that context is written down in docs, and reading through them is an early step in building a depth of understanding. Writing your own early docs works in a similar way: it shows you the gaps in what you thought you knew and forces you to look a layer deeper.

Impact over the first 100 days has come in waves: a stretch of learning and building support, then a push, then a pause to see what landed before the next one. The early waves are smaller, a few quick wins that show you understand the place. Once you've built trust and a deeper understanding of your role, the bigger waves of work follow on from there.

The value of in-person connection

At a talk to the product org, I asked Lenny Rachitsky what Stripe could learn from the other product teams he speaks with. His answer: Anthropic, and how deliberately they make time to be together in person. It stuck with me. In a remote-friendly world it's easy to default to calls, but I've tried to meet the people I work with face to face whenever I can. Trust builds faster, problems surface earlier and the follow-up conversations are better for this investment.

Focus on the craft

From the outside, Stripe is known for taking writing seriously, from its documentation and annual letters to Stripe Press. What struck me joining is how that external standard is mirrored internally in strategy docs, project updates and other internal written pieces. One of the best parts of the first 100 days has been learning from colleagues who care deeply about the quality of their writing and treat it as a craft worth sharpening. The culture of collaboration across documents sharpens the thinking behind every decision. The writing doesn't just make your thinking legible to others; practising the craft clarifies and improves the writer's thinking too.

"Skill in writing frees you to write what you want to write. It may also show you what you want to write."

Ursula K. Le Guin, Steering the Craft

More steering than rowing

One big shift I've noticed is in what product work actually looks like now. With AI, the distance between an idea and something you can build and test has shrunk. Much of the manual work you would have done yourself (the rowing) can now be handed to agents. The job becomes much more about steering: setting the direction, checking the output and adjusting course as you go. Just as the people I work with at Stripe have pushed my writing, they've also pushed how I use AI: moving past firing off reactive prompts when I have a question, to setting up agent workflows that run the repetitive tasks and pull me in as a reviewer. That shift, from prompting an agent to designing a workflow with yourself in the loop, lets you move and build at a speed that wasn't even possible until recent advances in models and AI tools.

If you're thinking about joining

A few people have reached out asking what it takes to land a Product Strategy & Operations role like this. People on the team come from a mix of consulting, product, strategy and ops backgrounds. The day-to-day leans heavily on structured problem solving, clear written thinking and comfort with data, alongside the AI fluency to build and automate your own workflows. Culturally, the traits that matter are high agency, a genuine focus on users and the flexibility to support where it matters most.

Conclusion

A hundred days in, I feel like I've found my footing, even if there's still a lot more of the business to learn. The first few months have really been about setting a pace, building context, earning trust and learning the craft from the people around me. If next year I'm still doing the exact same things I'm doing on day 100, something's wrong; as the company grows and you grow with it, the role is meant to change.