Don't Hire the Brilliant Jerk: A CTO’s Playbook for Building Real Teams

Commit & Push

"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.

If you enjoyed this episode, make sure to subscribe, rate and review on Apple Podcasts, Spotify and YouTube Podcasts, instructions on how to do this are here.

Episode Highlights:

• [0:00] Intro
• [1:03] Zach’s Journey to Becoming a Startup CTO
• [3:15] What is Gruntwork?
• [5:57] Balancing a Full-Time CTO Role with Coaching
• [6:50] Writing The Startup CTO’s Handbook
• [11:40] Lessons in Management and Hiring
• [16:22] Setting Goals & Metrics for Engineers
• [22:22] Full-Time vs. Fractional CTOs
• [28:12] Keeping Software Development Simple
• [30:51] Developer Productivity
• [34:50] Overhyped and Underrated Tech
• [44:43] Will AI Replace Developers?
• [49:38] Why Every CTO Should Consider Coaching
• [51:25] Where Can You Find Zach Online?

Episode Resources:

• Zach Goldberg’s Website
• Zach Goldberg on LinkedIn
• Gruntwork Website
• The Startup CTO’s Handbook
• Damien Filiatrault on LinkedIn
• Scalable Path Website