In this episode of Braintrust, Cortex co-founder and CTO Ganesh Datta sits down with Randy Shoup, SVP of Engineering at Thrive Market. Randy shares lessons from his leadership roles across multiple companies and explains how measurement and transparency can help teams build stronger engineering cultures.

Randy and Ganesh chat about how fear can block progress, why recovery speed matters more than trying to prevent every failure, and how teams improve through steady, incremental gains. They also discuss a few practical ways to build trust around metrics so organizations can use visibility for learning instead of punishment.

Steve Evans, former SVP of Engineering at Chegg, joins Ganesh Datta to explore why the microservices revolution created a new class of hidden costs that most engineering organizations never see coming. Steve shares his firsthand experience watching a 300-person org slowly get dragged down by an expanding empire of micro-repos, and why the real damage shows up not in outages, but in the cognitive tax on developers every single day.

Steve and Ganesh discuss why traditional engineering metrics like cycle time and deploy frequency can paint a dangerously misleading picture, how business context breaks down as it cascades through an org, and why round tables—not all-hands meetings—are the best way to diagnose where context stops flowing.

Jeff Schnitter, Solution Architect at Cortex and former developer experience leader at Workday, joins Ganesh Datta to explore why changing engineering culture requires starting with pain points rather than jumping to solutions. Jeff shares his experience shifting from a standardization mindset to an outcomes-based approach, the critical lesson that software development is "more faith-based than tech-based," and why new employees are uniquely valuable for questioning the status quo.