Brex 3.0: An 18-Month Operational Evolution & the Brex Hacker House “AI Startup within a Startup" experiment w/ James Reggio #236

Episode notes

James Reggio (CTO @ Brex) shares the story of "Brex 3.0", an 18-month journey behind their operational evolution. We explore how they rewound their org from a Series E to a Series C mindset, and replaced siloed OKRs with seasonal "marquee initiatives." James deconstructs the “Brex Hacker House”, an AI-focused startup within a startup experiment aimed to disrupt their core business. This conversation is all about evolving operational rhythms, layers of management, product building, and culture change! ABOUT JAMES REGGIO James Reggio is Brex’s Chief Technology Officer. James is a forward thinking technology leader who currently oversees Brex’s entire Engineering org. James joined Brex in 2020 as Principal Engineer and has played a vital role in building the company’s mobile app and AI capabilities. Prior to Brex, James had an extensive career as a Software Engineer at leading companies such as Microsoft, Salesforce, AirBnB, Stripe and more. Additionally, James founded two companies: Altair Management and Banter, a social discovery platform for podcasts that was later acquired by Convoy in 2018. James received his B.A. of Science from The University of Texas Austin.

• The Product Paradigm Shift: How Livekit Navigated High Stakes Scaling Challenges to Build the Future of Voice-First AI Interfaces w/ Russ d’Sa #26276 / 100
• Building an empowered career w/ Jean Hsu & Cate Huston #26163 / 100
• Redefining profit, centering human flourishing, and building an incorruptible mission-driven roadmap w/ Eric Ries #26075 / 100
• Affirm’s AI-native transformation & how it’s driving operational excellence w/ Geddes Munson #259
• Building reliable and proactive agentic systems at scale: how Shopify’s reflexive AI culture was instrumental in their development of Sidekick w/ Andrew McNamara #258