Brex’s AI Hail Mary — With CTO James Reggio

**James Reggio** (0:00)
We have like three pillars for AI strategy. We have our corporate AI strategy, which is how are we going to adopt and buy AI tooling across the business, and basically every single function to be able to 10x our workflows. And we have our operational AI strategy, which is how are we going to buy and build solutions that enable us to lower our cost of operations as a financial institution. And then the final pillar is the product AI pillar, which is like are we going to introduce new features that enable Brex to be a part of the corporate AI pillar of our customers. It's like we want to build features and be a solution that somebody else is saying to their board, hey, we adopted Brex and this is part of our corporate AI strategy.

**SPEAKER_2** (0:51)
Hey, everyone. Welcome to the Latent Space Podcast. This is Celestio from the Colonel Labs, and I'm joined by Swigs, editor of Latent Space.

**SPEAKER_3** (0:57)
Hey, hey, hey. And we're here with James Reggio, CTO at Brex. Welcome. Hey, thank you for having me. Thanks for visiting from up in Seattle, where I've been a little bit. It's cold up there, huh?

**James Reggio** (1:07)
Yeah, and we have an atmospheric river hitting the city right now, so a lot of it blowing. Yeah, well, yeah, we're getting the full-on winter effect right now.

**SPEAKER_3** (1:15)
Well, you're here to talk about the sort of AI transformation within Brex. There's a lot of interesting tidbits that we're going to draw from your article, but also your background. You have got a wide array of experience from Stripe to Banter to Convoy. And I think also mostly I'm interested in your journey as one of the rare people that have transitioned from like a mobile engineering leader to a CTO, which I think is also a bit more rare. I used to have this comment in the past where there's a career ceiling for people who work on client-only things where usually they don't hit CTO, whereas they typically promote the back-end people, the back-end clouding for people to CTO.

**James Reggio** (1:54)
Yeah, you know, it's something that I hear fairly frequently because there aren't that many folks with a front-end background who reach this level of leadership, and it's exciting for me to be able to represent that group. But I'll say that even though my resume kind of reflects that I've been more on the front-end of things, it's probably more my experience as a founder a couple times over that actually helped me get to this level of my career working for somebody else. Becoming CTO is very much like a leadership and general business role as much as it is a technical role. And so I think it was more the skills that I built from starting companies and trying to build those up made me a decent fit and enabled me to get the nod from Pedro to take this on as my predecessor left about two years ago.

**SPEAKER_3** (2:36)
Yeah, one thing I'm curious to you guys' commentary. This is a little bit broad, unscheduled, but a lot of startups are bragging about how many ex-founders they have. And yes, to some extent you want people with the founder mentality and agency, which is what you did, to be your employees and to take initiative in the company. But also I wonder if it's becoming anti-signal sometimes. I don't know if you've thought about this.

**SPEAKER_2** (3:00)
I think it's more about the turn for me, especially when people are hiring ex-founders is like if you're truly of the founder gene, it's kind of hard to just stay somewhere. It's like an IC for too long. And then it's like, all right, I joined this thing and then in one year, I'm back to being a founder. I'm curious for you. Yeah. What was your I'm sure you thought about leaving and like doing another company.

**James Reggio** (3:20)
In fact, that was that was the alternative I was considering even at the time that I got the phone call where they made me the offer to become CTO, I was thinking about leaving to go start a company. And you know, I think what's interesting about it, we actually launched sort of like a new recruiting and employee value proposition for Brex a couple months ago called Quitters Welcome where we actually intentionally are leaning into this idea that we have a disproportionate number of folks who go on to become founders or like heads of a department when they leave our company and we celebrate that. It's actually something that I'm very proud of. And that means that like we we welcome in people who want to get a different experience. I think that there's certainly like a lot of founders who don't make it don't scale their own businesses to this to the scale that we've achieved at Brex. So there's something to be learned when they come in. And then we're very happy to like support people on their way out. And so I actually really like hiring former founders or future founders. The one value proposition I find that's most relevant because a lot of the folks we're hiring as AI engineers are kind of folks that are either like finding out their companies or considering maybe running AI startup. The thing that resonates the most with them is that we oftentimes can give them problems to solve that are interesting, problems that maybe they even want to want to like build their own startup around, but with instant distribution.