Current Role: Staff Product Manager, Stripe Terminal
What do you do? I work with a team to build developer interfaces that enable money movement in-store
Years in career: 12
Undergraduate major: Physics
Let’s start with the beginning of your career. What was your first job out of college?
In college, I was really drawn to finance—specifically buy-side investing. I liked the idea that you could make bets on a company’s strategy and be rewarded for being right. I had some offers from traditional investment banking roles, I was actually drawn to a lesser-known group at Wells Fargo that did principal investing. It was small and focused on high-yield debt. I thought, why not skip the sell side and go straight to the buy side?
Honestly, it was the interview that convinced me—I got these really interesting puzzles like, “Tear down this company and tell us if it’s a buy or sell.” That was the kind of work I wanted to be doing.
And at some point, you made the jump to tech. Why?
I started to realize the part I loved about investing was the deep dives—talking to industry insiders and understanding strategy. It wasn’t about turning money into more money. I wanted to be hands-on. Since I covered tech and had a physics background with some coding and data skills, moving into tech made sense to me.
Looking at roles that didn’t obviously interest me helped me stay curious and kept the stakes low.
How did you get your foot in the door?
I had to put myself out there in ways that felt uncomfortable. I went to mixers, reached out to friends of friends of friends—sometimes pretty distant connections. I cast a wide net because I believed every conversation added something, even if it didn’t directly lead to a job.
It felt fruitless at times, but it’s a funnel game. You go broad and eventually, you narrow in. Looking at roles that didn’t obviously interest me helped me stay curious and kept the stakes low. It wasn’t about turning every conversation into a job offer. It was about learning. All in all, I probably talked to more than 50 people over six months.
I also had to frame my experience to prove that I had the skills. For example, I’d explain how pitching a billion-dollar investment to a portfolio committee is like influencing cross-functional teams. You’re trying to convince someone the direction is right and adapting based on their input.
What job did you end up landing?
A solutions architect/integration engineer at AppNexus, an ad tech company. Not quite product, but it was technical and user-facing.
I call it a “square peg, round hole” role. The product was designed to do one thing, users wanted something slightly different, and I was the layer that made it work. It gave me deep exposure to user pain points and technical complexity.
How did you move from there to Stripe?
Stripe was starting a New York office and had a similar role. I was actually interviewing for PM jobs elsewhere, but I was so intrigued by Stripe that I decided to choose the company even if I wasn’t going to do product right away.
I believed that to be a good PM, you have to really like the product. With ad tech, even our execs had ad blockers. Stripe was different. They were making entrepreneurship more accessible, and it felt like everything I’d done in finance and tech up to that point came together.
How did you eventually bridge the last mile to product?
I always tried to go a couple layers deeper to understand why the product was built a certain way and how user needs aligned with that. That made me a strong partner to the product teams. A year in, one of the product teams I worked closely with asked me to join as a PM to lead global expansion. Ultimately, it was a slower path, but one that felt authentic to me.
I’d walk into leadership meetings thinking, I shouldn’t be here, they won’t get it.
What challenges did you face after you finally got into product?
Two years in, I hit a plateau. I was doing complex work, users were happy, but leadership didn’t really get it. I had this “us vs. them” mentality—thinking, I’m doing important work, but it’s too complicated for others to understand. That was demotivating.
What changed?
I had a great manager who believed in me. Other managers had told me I lacked storytelling skills, but he found the good parts in my communication and helped me grow from there. That gave me the confidence to keep pushing forward.
Before that, I’d walk into leadership meetings thinking, I shouldn’t be here, they won’t get it. That was already painful—so transforming my communication style, even if it was hard, wasn’t more frustrating than staying stuck.
What’s some of the best career advice you’ve received?
That corporate writing is the opposite of creative writing. In creative writing, you build up to a narrative climax. But in corporate settings, execs want the point up front. What do you need from me, right now?
Once I started leading with the bottom line and framing the ask before the context, I became much more effective. And now I get why my earlier style didn’t land. It wasn’t poorly written—it just wasn’t effective for the audience.
There’s a difference between what you do and what you are.
How has your relationship with your career changed over time?
My career has always been a source of pride—even when I was in the wrong role or industry. What’s changed is how I relate to it emotionally. A manager helped me see that there’s a difference between what you do and what you are. I can be proud of solving a hard problem. But if I haven’t solved it yet, that doesn’t change who I am. I’m still a problem solver. That shift has helped me take a less emotional lens to my work—and bounce back faster from setbacks.
Thank you Jessica for sharing your story!
Joyce Lin Coaching 
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