Can You Trust AI With Payroll? with Gabe Monroy

In this episode of The Bear Roars, Dan sits down with Gabe Monroy — Chief Technology Officer of Workday — for a candid conversation about building AI you can actually trust in the highest-stakes corners of the enterprise: people and money.

Gabe reflects on a career spent at the center of modern computing — helping shape the container and Kubernetes technology that quietly powers nearly every major AI system today, standing up the container and distributed compute businesses inside Microsoft Azure, and serving as a product and engineering leader at DigitalOcean and Google Cloud before taking the CTO role at Workday, where roughly 70% of the Fortune 500 are customers. He explains why he walked away from the world of runaway AI infrastructure spend after sensing a "bubble-ish" disconnect from reality, and why the real opportunity is solving AI where a mistake isn't a bad chat response — it's a missed payroll or a broken ledger.

They get into how AI is reshaping engineering itself — from swarms of agents that let two people ship in a week what once took sixteen engineers six months, to why "taste" and systems thinking now matter more than specialized skills. Gabe makes the case for deterministic guarantees over probabilistic magic, why open-weights models are becoming a critical counterbalance for enterprises wary of a government "kill switch," and why he believes Colorado has every right to lead the next era of innovation — if it leans into the change instead of legislating against it.

Learn more about Workday: https://www.workday.com

Order Dan's Book – Bandwidth: The Untold Story of Ambition, Deception, and Innovation that Shaped the Internet Age and Dot-Com Boom: dan-caruso.com/book

To nominate a founder or yourself as a future guest speaker, email: contact@loudbearproductions.com