In this episode of the groCTO Podcast, host Kovid Batra is joined by Ben Matthews, Senior Director of Engineering at Stack Overflow, with over 20 years of experience in engineering and leadership.

Ben shares his career journey from QA to engineering leadership, shedding light on the importance of creating organizations that function collaboratively rather than just executing tasks independently. He underscores the need for cross-functional teamwork and reducing friction points to build cohesive and successful teams. Ben also addresses the challenges and opportunities presented by the AI revolution, emphasizing Stack Overflow’s strategy to embrace and leverage AI innovations. Additionally, he offers valuable advice for onboarding junior developers, such as involving them in code reviews and emphasizing documentation.

Throughout the discussion, Ben highlights essential leadership principles like advocating for oneself and one’s team, managing team dynamics, and setting clear expectations. He provides practical tips for engineering managers on creating value, addressing organizational weaknesses, and fostering a supportive environment for continuous growth and learning. The episode wraps up with Ben sharing his thoughts on maintaining a vision and connecting it with new technological developments.

💡 Highlights

a) Getting Candid

📈 Journey from QA to Senior Director at Stack Overflow

🎿 Snowboarding enthusiast, calzone lover, and movie buff

🤝 Advocates for collaboration, emphasizing that tech is a “team sport”

b) Key Takeaways

💡 Crafting cohesive teams by reducing friction

🤖 Staying ahead by embracing AI at Stack Overflow

📘 Effective onboarding & mentoring of junior developers

🔑 Ben’s top 3 leadership principles for success

📊 Unmissable advice for Engineering Managers

🎧 Full Episode

This episode is also available on YouTube, Spotify, iTunes/Apple Podcasts, Amazon Music & more.

Thanks for listening to the podcast. That’s it for today 👋

1) Subscribe to groCTO — If you aren’t already, consider becoming a groCTO subscriber.

2) Share amongst fellow Engineering Leaders and CTOs! Your referral empowers & builds our groCTO community.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit grocto.substack.com

12.12.25 Clark Answers His Critics on Clark Stinks / Retirement Planning 2026

The Clark Howard Podcast

Clark Stinks: Listener Critiques Begin

The AI-powered Podcast Player