Episode

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

Podcast: The Engineering Leadership Podcast
Published: Nov 12, 2025
Duration seconds: 2730
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Summary

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!