Seven years at Stripe

Seven years ago today, I walked through the front door of Stripe.?Patrick Collison?held the door open for me—literally and figuratively. He was simultaneously walking and reading a huge white book and welcomed me in.?It was my first job in tech and I was sweating bullets, which was very visible due to my poor wardrobe choice of a white shirt. And it didn't help that the CEO was the first Stripe I met!

I first heard about Stripe when I was building a website for a political campaign. It wasn’t PCI-compliant—I was storing the full card numbers. When we hired a real developer to redesign our site, they said to use Stripe. I read?stripe.com/docs?and fell in love.?I did some more research and saw?Claire Hughes Johnson?talk about how political campaigns are a great training ground for startup life, speaking from her own experience. She said that startups were 1) constantly fundraising, 2) moving quickly, and 3) couldn’t afford to make missteps.

I applied at?stripe.com/jobs. I thought I'd be one of the first to join Stripe after using Stripe, but turns out, many, many preceded me and even more followed. (Which I thought was reflective of our user-focused mentality.)

One of my primary responsibilities was to answer any user’s question that was tweeted. (And sometimes,?Patrick Collison?would anonymously help from @stripe too!) I came to work each day with no idea what would be asked—from “how do I sign up” to “how do I integrate Connect?”?Handling support was the best way to learn the product, and it still is today. I try to talk to users each week. In dealing with intangible APIs, I've found humanizing the user experience useful—talking to users helps inform nearly every decision we make.

For example, sitting next to a user as they used the Dashboard helped us remove clicks in getting started with subscriptions.?Or hearing exactly how slow bank transfers affected a solopreneur’s weekly food budget helped us launch Instant Payouts.

I’ve also found working at Stripe hard—I don’t think I’ve ever been in a room where we decided to not do something just because it was too hard.?In fact, I love when the harder path is chosen just for the sake of being hard—so the path can be better paved for those behind us.?If a user got locked out of their Stripe account, I’d call them right away. One Saturday, I saw a user tweet about getting locked out, then helped them while in the noodle aisle of 99 Ranch. It set the precedent for weekend account lockout support, which dozens now staff.?On a whim, a few of us decided to review YC applications and helped one founder get into YC. Today, hundreds of Stripes now volunteer to help with this—and they’ve helped hundreds of founders get into YC. As?Patrick McKenzie?puts it:?https://twitter.com/patio11/status/1369039739718828036.

These microdecisions seemed inconsequential at the time—quick one-off things. But as an early employee, they can set the pace and direction for the thousands of employees after. They were rooted in that users-first mentality, which can penetrate a deeper cultural layer.?They’re built upon by others and its effects are longer than imagined. Being open to their potential trajectory and evolution—and making that an assumed job responsibility—I think, was helpful.?Imagine when flying: a one degree change in heading, once flown for hours, can set you hundreds of miles away from the initial plot.

Today, as I enter my eighth year, I get increasingly asked, “Why are you still at Stripe?”?

1. When I read?stripe.com/docs?now I recognize the wider breadth of impact we can have on businesses today.
2. When I meet with users I realize we're even more critical to their potential success.
3. When I talk to Stripes I believe that we are still making these "early" microdecisions today. The final heading of Stripe—and the economic landscape it impacts—has yet to be set.