Commit & Push
Don't Hire the Brilliant Jerk: A CTO’s Playbook for Building Real Teams
July 10, 2025
Most software sucks. Most performance reviews are broken. And most new CTOs are flying blind. In this episode of Commit & Push, Damien sits down with Zach Goldberg—CTO of Gruntwork and author of The Startup CTO’s Handbook—to unpack the real challenges of building and scaling a dev team. From metrics that actually matter to avoiding productivity traps, Zach shares pragmatic strategies every tech leader should know. Whether you're running a growing team or just trying to avoid the usual mistakes, this episode cuts through the fluff and gives you the straight-up roadmap to doing it better.
"Don’t hire the brilliant jerk." That’s just one of the hard truths Zach Goldberg, CTO of Gruntwork and author of The Startup CTO’s Handbook, drops in this episode of Commit & Push.

Zach joins Damian to talk about the mistakes most new CTOs make, why developer productivity is wildly misunderstood, and how overcomplicating your stack can tank your team. They dig into what actually works when scaling a dev org, how to build real performance systems, and why most software out there… just isn’t very good.

If you're leading engineers—or thinking about how to lead better—this episode is your shortcut to avoiding expensive management lessons and building a team that actually ships.

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