How Shared Roadmaps Improved Morale

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.

SHOW NOTES:

• The birth of Brex 3.0: Using a layoff as a "moment to refound the company" (3:38)
• Moving from a Series E to a Series C operational mindset (5:28)
• The problem with a GM model: How siloed OKRs and roadmaps created "deadlock" (6:07)
• New rituals: Why the CEO became "chief editor of the roadmap" (8:16)
• The impact on morale: "Folks just knew how their work fit into the bigger picture" (11:16)
• The challenge of the new model: Who do you hold accountable when you "win and lose as a team"? (13:43)
• The lesson for reintroducing systems: "Less is more" (15:43)
• The "Startup within a Startup": Launching an internal team to disrupt Brex (16:49)
• “What if we were founding Brex again today?” The 4 constraints for the "Hacker House" experiment (17:58)
• Questions eng leaders should ask when running a similar experiment to Brex (21:02)
• Aha moment: "With agentic coating, code is so cheap" (22:35)
• Managing the two narratives: "compounding" the core biz vs. “innovating" with AI (26:01)
• A surprising dynamic: Why the AI team struggled to see their impact (while the core team didn't) (29:38)
• Building alongside your customer to iterate / experiment faster (36:06)
• The turnaround is over: Brex hits 50% YoY growth and cash-flow positive (38:45)
• Rapid fire questions (42:10)

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

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