Principle 5 — Co‑working with AI

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What if your biggest advantage as a CTO has almost nothing to do with technology at all?



In this episode, I sit down with Rory Herriman, US CTO at Zip Co, whose thirty year career runs from the military through large enterprises to high growth fintech. Rory brings a playbook forged in real world pressure, from learning to stay calm under fire to realizing that the job is as much about business impact as it is about systems and code. That journey taught him to care less about flashy problems and more about culture, fundamentals and the people he is working with every day.

We get honest about what it feels like when you're the one carrying the unspoken weight of every decision while everyone else assumes you've got it handled. It is very easy to slip into chasing hype or focusing on the wrong signals when the real leverage is in resilient fundamentals and a clear link between decisions and business impact. We explore what it actually looks like to stand on that bedrock, keep things fluid around your people, and lean into a near-term future where humans and AI are working side by side. And you'll see why leading this way makes the CTO journey feel a lot less lonely and a lot more sustainable.

You’ll Learn:

[00:00] Introduction

[04:14] How military calm under pressure becomes one of a CTO’s most transferable advantages

[08:02] Why the real job isn’t technology but understanding business impact at a deep level

[13:03] What shifts when you stop being the smartest technologist and start leading through people

[17:06] The humbling moment that proved one org chart can’t fix cultural differences

[19:48] Why a strong bedrock of fundamentals makes everything else faster and easier

[24:58] How treating people and systems as symbiotic unlocks execution instead of friction

[28:54] The power of fluid teams that move to the work rather than waiting for work to come to them

[33:04] What changes when a CTO stops chasing the future and starts shaping it

[46:12] The reason AI isn’t cost-cutting, but a resource multiplier that expands what humans can do

[50:28] What hybrid human + AI teams look like inside an organization right now

[55:02] Why excellence, velocity and integrity aren’t trade-offs but a three-part operating balance

You can connect with Rory and his work on his LinkedIn and his website.

Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.