As AI reshapes the what of engineering, leadership is about focusing on the who.
This week on High Output, Glenn Veil, SVP of Engineering at Order.co, shares how three decades of unplanned leadership taught him the most important lesson of all: technology will always evolve—but people remain the constant.
Glenn didn't start out aiming to lead. One sudden promotion, a broken website, and a confused loft full of engineers later, he found himself in charge—and completely unprepared. What followed was a trial-by-fire journey from tech-first problem solver to people-first builder of teams, careers, and future leaders.
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What's inside (23 min):
→ The accidental promotion. Glenn thought he was getting fired when the VP was waiting for him at the front door. Instead: "Glen, you're director of technology." He had to tell his new team: "Hey, I think I'm in charge now."
→ The hard lesson: people over code. Glenn started by focusing on what he knew—the technology. But he learned that engineering leadership isn't about fixing code; it's about developing the people who write it.
→ The great wave of leaders. Glenn's mission today: leaving behind a generation of engineering leaders who know they can succeed by being authentically themselves.
→ Reading people, not trends. His secret to staying ahead isn't predicting the next great technology—it's anticipating how people and teams will evolve through change.
Why it matters
As AI handles more of the technical heavy lifting, a counterintuitive truth is emerging: the human side of engineering leadership becomes exponentially more valuable.
Glenn's prediction is already playing out—companies will operate at dramatically lower costs within five years as AI optimizes processes. But the real competitive advantage won't come from deploying the smartest AI tools. It'll come from using those tools to create space for deeper people development.
Smart engineering leaders aren't just automating code—they're choosing AI solutions that help them understand their teams better, spot growth opportunities faster, and develop the kind of human leadership capabilities that no algorithm can replace.
As Glenn puts it: "I don't think we'll ever not need software engineers. But we will be leaner. And we'll need stronger leaders to guide the way."
The question isn't whether to adopt AI tools. It's whether you're choosing the ones that multiply your people's potential—not just their productivity.
Your turn
Glenn's approach raises the critical question: How are you using AI's efficiency gains? Are you reinvesting that time and mental bandwidth into developing your people—or just pushing for faster delivery cycles?
If you're ready to move beyond productivity theater and start building the kind of human leadership capabilities that will define tomorrow's engineering orgs, we'd love to hear your story.
Schedule a chat with us → https://cal.com/team/maestro-ai/chat-with-maestro
High Output is brought to you by Maestro AI. If you're an engineering leader looking to improve velocity while using AI efficiency gains to develop stronger teams, visit https://getmaestro.ai to learn how we help teams navigate the future of software development.
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