James Reggio

Chief Technology Officer at Brex who led the Brex 3.0 operational evolution and launched an internal AI-focused 'Hacker House' startup experiment; former principal engineer and founder with prior roles at Microsoft, Airbnb, Stripe and others.

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Nov 12, 2025 • 46min

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

James Reggio, the CTO of Brex and a former engineer at Microsoft, Airbnb, and Stripe, dives into Brex 3.0—a bold operational evolution. He shares how a layoff sparked a rebirth, reshaping the company’s focus from a Series E to C mindset. Discover the innovative 'Hacker House' initiative, a startup within a startup aimed at AI disruption. Reggio discusses the introduction of seasonal initiatives for alignment and how shared roadmaps have boosted morale. His insights on balancing innovation within core operations are both enlightening and actionable.

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