2024-06-14
"Understanding how you feel in the face of other voices is the most important skill for an artist to practice"
— Rick Rubin
tl;dr — I’m joining Stripe!
It was a long (winding) road to get here. And it wasn’t the obvious choice when I started my search. So I wanted to share how I thought about it, and why this ended up being the perfect opportunity, in hopes that it helps someone else navigate their own journey [1].
I believe careers are like games, not ladders. This means I rarely take the next logical step (yet I’m always tempted to). I start every process by going wide, talking to as many people as I can. Then at a certain point, I hit pause and switch to synthesis. I sit with everything, digest it, and just reflect. I find writing snippets out on paper and physically arranging them around me to be the most helpful tactic in these situations. From this I’m able to develop a framework that is specific to where I am in life (or to continue the metaphor, the game I want to play).
For my next chapter, I boiled everything down to 5 things.
Purpose: I need to feel good about the work I’m doing. I need to know it’s a net positive on society (without squinting). Stripe is growing the GDP of the internet. Stripe is empowering anyone (seriously, anyone) to participate in the economy. I loved this feeling at Square, and Stripe is doing it on steroids.
Talent: It’s almost trite to say “I like to work with smart people”. Instead, I’ll say I like to work with people who intimidate me. I like to work with people who humble me. I like to work with people where the only reaction you have after a conversation is “wow, that person is on another level”. Well, that was every conversation at Stripe (including the ex-Stripes I backchanneled with) [2]. I want to feel the discomfort of not being good enough everyday (and slowly becoming good enough, day by day).
Craft: I think I care about design more than the average person. And I do my best work in environments where quality is an expectation, not a goal. I need the company brand and great design to be synonymous. To me, Stripe embodies that in several aspects. Patrick talks about craft & beauty a lot. His deep care for it came through in my conversations with him, as well as the rest of the team. It felt like my tribe.
Stories: I like to work. My ideal retirement plan is teaching and advising. When I think about what is required to be a great teacher and advisor, I think of stories. Stories are my currency for life. Stories are how you learn, how you share, how you bond. Despite their existing success, Stripe is at the 1-yard line. And it became apparent that the upcoming years would provide me with the richest stories I could imagine [3].
Role fit: I recently mentioned how at a certain point in your career you start looking for you-shaped roles. Things that don’t make sense to most people but seem like a tailor-made suit for your particular skills and experiences. When Stripe reached out, the role felt like a sweater I used to wear that was one size too small. But as we continued talking, they evolved the role. It changed in shape and size. Eventually, I couldn’t take my eyes off of it. It leveraged my experience at Square. It leveraged my growth as an exec over the past 3 years. It leveraged my innate zone of genius [3]. And after enough reverse interviews, I was able to understand the vision and built enough conviction that I would be supported to act on it.
Okay, okay, okay…tell us what you're doing already!
My official title will be Head of Product, Merchant Experiences. Simply put, my job will be to help more Stripe users get more value from our UIs (not just our APIs). So if you ever have any issues or thoughts on how the Stripe Dashboard / mobile apps could be better, shoot me a message at yien@stripe.com :)
This role was particularly exciting because of the evolution Stripe is going through. They have been known as an API company for the majority of their life. But as they expand into new customer segments and value props, more and more value will come from people using their web/mobile products (like Dashboard!). Layer on the obsession with craft & beauty and you can start to see why this was a no-brainer.
There is a lot more to share (and in due time, I will). But I hope this helps some of you gain clarity on how to approach your next adventure. And if my reasons for joining Stripe resonated with you, shoot me a message — we’re hiring.
[1] This post focuses on the “logical” side of things. There is another post I should write that focuses on the “emotions”. This is often the most challenging part about making career decisions. But it would have muddled the message too much. If you’d be interested in reading more about that, send me a message.
[2] I cannot recommend backchanneling with current and former employees of a company more. You get the roses and thorns. If you don’t have a direct connection, there’s usually some secondary connections you can get from LinkedIn who will at least respond to a few questions over email. Plus there’s always Jeff Weinstein who seems to respond to every Stripe question ever.
[3] Everyone will have their own definition of what a “rich story” means. I needed a scale that was unique (Stripe is processing over 1% of global GDP at this point). I needed leadership who cared deeply about quality (every interview probed me on this). And I needed relevance (users I could relate to and talk about with anyone).
[3] Zone of genius is a really helpful concept that the CEO of Mutiny (Jaleh) shared with me. She helped me refine my understanding of various zones better than I could alone. If you’ve never done this exercise, I highly recommend reaching out to old managers / coworkers to triangulate a version for yourself. They can often offer a clearer perspective (especially on the zone of genius) than you can alone.