Brex’s AI Hail Mary — With CTO James Reggio
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What is Brex’s three‑pillar AI strategy and why does it matter?
We have like three pillars to our AI strategy. We have our corporate AI strategy, which is how we're going to adopt um like buy AI tooling across the business and basically every single function to be able to 10x uh our workflows. And we have our operational AI strategy, which is how are we going to buy and build uh 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 uh that um 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 a a solution that somebody else is saying to their board, Hey, we we adopted Brex and this is part of our corporate AI strategy.
Hey everyone. Welcome to the Laden Space Podcast. This is Celestio from their Colonel Labs and I'm joined by Swix, editor of Laden Space. Hey, hey, hey.
And we're here with Jason Regiosi to our Brex. Welcome. Hey, thank you for having me. Thanks for visiting uh from up in Seattle where uh I I've been a little bit. It's cold up there, huh?
Yeah, and we have an atmospheric river hitting the the the city right now. So a lot of yeah, well yeah, it's uh we're getting we're getting the full on winter effect right now.
Well
you're you're here
We talk about the sort of AI transformation within BREX. There's a lot of um interesting tidbits that we were going to draw from your article, but also your background. You have got a wide array of experience from Stripe to um banter to convoy. And uh I I think also mostly I'm interested in your Journey as is 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 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 the back end people or the back end clouding for people of the CTO.
Yeah, you know, it's it's something that I I f hear fairly fairly frequently because um 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 I'll say that even though my resume kind of reflects that I've been more on the 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 this level of my career working for somebody else, becoming the CTA. Yeah, it was very much like a leadership and and like 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 and trying to build those up made me a decent fit and enabled me to get the nod from from Pedro to take this on as my predecessor left about two years ago.
Yeah, uh one thing I I'm curious 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 what you did, to be your employees and to 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. I think it's more about the turn for me, especially when people are hiring ex founders. It's 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. Uh 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.
In fact, that was that was the 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 uh, you know, I think what's interesting about it, we we actually launched um 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 uh we have a disproportionate
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Chapters
5 chapters
1
What is Brex’s three‑pillar AI strategy and why does it matter?
0:00–9:36
2
How did James transition from a mobile‑engineer to Brex’s CTO?
9:36–21:20
3
Why does Brex let employees build their own AI stack instead of picking a single vendor?
21:20–44:44
4
How do SOP‑driven agents outperform over‑engineered reinforcement learning in finance operations?
44:44–1:06:52
5
What does Brex’s internal AI platform (LLM gateway, prompt management, evals) look like?
1:06:52–1:13:16
Speakers
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