Leading with Curiosity: What Makes a Great Tech CEO

The Tech Trek

In this candid conversation, Bryan Mahoney unpacks his journey from CTO to CEO, exploring what it really takes to evolve beyond the engineering org into leading an entire company. We talk about how his curiosity and hands-on technical skills still shape how he leads today, the mental shifts required to manage AI-driven teams, and how leadership demands evolve as a company scales from services to SaaS.

Along the way, Bryan reflects on AI’s role in shaping engineering culture, the future of career ladders, and the illusion of control in modern software development. If you’ve ever wondered what it means to be a modern tech CEO—or how AI is transforming the very DNA of how we build software—this one is for you.

🔑 Key Takeaways

Accidental CEO: Bryan didn’t set out to become a SaaS CEO—but by leaning into opportunities, he transitioned from a hands-on engineering leader to running a product company.

Curiosity Over Playbooks: Rather than relying on frameworks, Bryan values curiosity as the anchor for decision-making and adaptation, especially in fast-evolving areas like AI.

Engineering Culture in an AI World: Bryan believes AI won’t eliminate engineers—it will amplify those with experience and curiosity. Promotions may speed up, but depth still matters.

Reframing Control in AI Workflows: AI doesn’t remove human control—it shifts it upstream. Engineers become managers of agents, not just code.

The Future of Tech Debt: With strong test coverage and agent support, code may become more disposable. The future of engineering may prioritize outcomes over sacred codebases.

🕰 Timestamped Highlights

00:00 — Intro and Bryan’s path from CTO to CEO

01:43 — His early entrepreneurial background and how Cord “accidentally” became a SaaS company

03:21 — The new skills Bryan had to learn: go-to-market, packaging, and investor relations

06:53 — Why mental models grounded in curiosity matter more than fixed frameworks

09:41 — Staying close to the codebase and why technical empathy gives CEOs an edge

13:22 — AI and the future of engineering ladders: what’s changing and what still matters

18:11 — Could code become disposable? Bryan’s thoughts on AI and tech debt

22:37 — The overlooked challenge: AI may help ship fast, but who’s thinking about maintainability?

24:01 — Engineers as agent managers: redefining accountability in AI-assisted dev work

26:16 — Hollywood glamorized AI, but Bryan reminds us humans are still at the center

💬 Quote of the Episode

“You're still in control. You're not giving it up—you're shifting it. We all need to be managers, not of humans, but of agents.” — Bryan Mahoney

🧠 Career Tips (discussed in episode)

Don’t rush the title: Career progression in engineering should be thoughtful. Output may scale faster with AI, but real impact still requires experience and context.

Upskill across functions: Moving from CTO to CEO means learning sales, go-to-market, and investor relations. Bryan did it by staying curious and surrounding himself with experts.

Stay hands-on if it fuels you: Writing code helped Bryan stay grounded, understand his team better, and maintain technical credibility as a CEO.

📚 Resources Mentioned

Glossier’s Engineering Career Ladder — Bryan open-sourced this while at Glossier. It’s still a great reference for thinking through growth in engineering orgs.

Contact Bryan —

📧 Email: [email protected]