Jean-Denis Greze: CTO of Plaid, the $18B Fintech Startup; How to Hire, Fire & Build Great UX | E1038

There's great hiring and there's great firing. One of the things you realize about founders is first time founders, they don't realize they have to be great at firing. They just think they have to be great at hiring. But you have to be great at realizing when your talent's not working out and identifying that and working with them and moving on. And initially, founders don't do it early enough, and then they learn their lesson a few times and then get really good at it.

Jean-Denis, I'm so excited for this. I heard many good things before we started the conversation. So thank you so much for joining me today, first.

Cool. Thank you, Harry. I'm super excited to be here. I, I feel like, uh, I'm, I'm getting the benefit of, uh, being on here more than you're getting the benefit of having me on the show. But, uh, I'm excited to do my best to impress.

Well, I'm about to extract a decade of knowledge, so I think I'm the one winning. But I want to start with your career. And I think careers are often made actually with more singular moments. So when you reflect, what would you say was the single biggest break in your career, and how did it impact your trajectory?

That's a good question. I think... Look, I think objectively the answer would have to be joining Plaid as, you know, to, to lead engineering, um, which was about six and a half years ago, just because I joined when the company had, you know, 40-ish people, and, you know, less than $10 million in ARR. We've had f- we've had a crazy trajectory. And it means, like in terms of my career and my ability to be successful long term, I have a lot of options now that I never would have had if I hadn't joined Plaid. But actually, it's not... Joining Plaid is not what I consider the, the lucky break that I had. That would be joining Dropbox, which was my first job like truly in Silicon Valley. Um, yeah, so before, before Dropbox, I kind of had a weird career. I worked in tech for a bit, and then I'd been a lawyer for a bit. Then I helped a friend kind of grow a company, like a fintech company in New York, but more on the hedge fund side of things. And I hadn't had, like what you would call like a triple A employer on my resume. You know, I was smart, but, you know, I was kind of a weird outsider with, you know, a little bit of an attitude. And I realized at some point that if, if you want to be an engineer and you want to do great engineering work, at the time at least, I felt like you had to move to Silicon Valley. And I was in my early 30s. You know, I don't think I'd had a great success. And I knew a friend at Dropbox, and so he got me in the pipeline to apply. And, you know, I applied there, and I, I know 'cause they told me after the fact, I actually didn't do that well on the interviews. I did well on half of the interviews, and I didn't do well on, on the other half of the interviews, especially on some of like the people skills and, you know, I think I came across as a little too smug and, and sure of myself. And there's two people at, at Dropbox that saw something in me during the interview process, uh, this guy Albert and, and this guy Ramesh, and they, they went to bat for me. Um, and, and they, you know, they, they were like to me like, "Maybe we'll structure it as like, like an apprenticeship where you, like join for a few months and we see how it works," and whatnot. And they were like, "Look. No, listen, like we should hire this guy. He's got some spikes. Like he's weird, but that's what we need at, at the company." And a lo- I'll give a lot of credit to the culture that Drew and Arash, the founders, created. Like I think Dropbox was very good not just at getting the standard talent, but at, like looking at people that weren't quite conventional that they thought could really accelerate the business. And I'm, I'm ex- like eternally thankful for it, 'cause, you know, after that, you get Dropbox... People don't realize now maybe, but Dropbox, like 2010 to 2017 on your resume, that really just opened all the doors. And I learned a ton there. It was an amazing company, amazing talent, uh, and I think it's, you know, it admitted that I can keep working here for a very long time.