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I wrote about my experiences working at Stripe for the last 4 years: https://kalzumeus.com/2020/10/09/four-years-at-stripe/
It's partly self-reflection, partly my view on why this is an extremely special company, and partly my continuing search for an answer to the question "So what is your *actual job*?"
It's partly self-reflection, partly my view on why this is an extremely special company, and partly my continuing search for an answer to the question "So what is your *actual job*?"
I think the biggest thing I've learned about myself from the experience is through reflecting, often with @taylorfrancis (then my manager, and a person more people should know) , on what I really want to get out of my career.
Since 2006 I had been mostly punting on that question. I was running companies! Success for the company is success for the career definitionally, right?
But anyone who knew me could tell you I got a lot more fulfillment out of writing, business mechanics, and helping entrepreneurs than I did out of the thrilling adventures that were PDF layout optimization and selling to dentist offices.
The thing I realized is that the through line of all the career things that gave me joy was helping software people be more successful. So I've made that more of an explicit focus, and it both helps pick the right opportunities and makes my work more meaningful to me.
I'm almost positive I'll run another company again someday, but for the moment Stripe seems to be an incredibly leveraged opportunity to help software people.
Like I told them at the interview: "You don't have to convince me; I fed my family out of a Stripe account for 6 years."
Like I told them at the interview: "You don't have to convince me; I fed my family out of a Stripe account for 6 years."
Pick customers you like dealing with because their problems will be your problems every day for forever. We have the best customers one could ask for: passionate, driven, smart people who are trying to claw something out of the ether. Working in the service of them is a delight.
It also has some formidable challenges. Stripe will someday be, if we execute correctly, one of the world's most important software businesses.
This doesn't mean that we have a magic wand around challenges inherent in getting thousands of people to work together.
This doesn't mean that we have a magic wand around challenges inherent in getting thousands of people to work together.
We're in those awkward teenage years between "We're a startup, so if we screw up, the blast radius will be pretty minimal" and "We're an extremely sophisticated enterprise, so clearly somebody has long-since solved X challenge + there's a process on it which repeatably succeeds."
This means that getting work done often requires subjectively more effort than it should, and sometimes things get a little nailbiting.
And the biggest risk isn't even screwing up. The biggest risk, by far, is getting complacent.
And the biggest risk isn't even screwing up. The biggest risk, by far, is getting complacent.
I am extremely fortunate to work with the folks I get to work with, and also the several team members who have gone on to new adventures after overlapping.
Stripes tend to be extremely smart, empathetic (almost to a fault), and purposeful about how they go about executing.
Stripes tend to be extremely smart, empathetic (almost to a fault), and purposeful about how they go about executing.
There is a metric shedload of work yet to do. At about 3,000 people, we're understaffed. We are hiring aggressively.
If you want to work on extremely worthy challenges, in the service of entrepreneurs all over the Internet, with very good colleagues: https://stripe.com/jobs
If you want to work on extremely worthy challenges, in the service of entrepreneurs all over the Internet, with very good colleagues: https://stripe.com/jobs
