The Seasoned Tech Leader Who Went Back to School — And What He Learned
If you look at Chris Bunk’s résumé, you’ll see an undeniably impressive track record. Current CPTO at FastSpring. SVP of Engineering at WorldPay. Years of leadership across fintech and enterprise technology. His is the kind of career arc that earns you a seat at the table…without having to prove much of anything anymore.
But there’s one entry that stands apart. One you probably won’t find on even the most decorated technology leader’s CV: a one-year sabbatical devoted to AI learning and discovery.
In 2024, Chris took something like a gap year. Not to decompress, not to consult — but to go fully hands-on with AI development tools because he believed the moment was simply too significant to experience from a distance. Cursor. Windsurf. Eventually, Claude Code. He went deep, built things, joined communities of like-minded senior technologists doing the same, and emerged with something most CTOs at his level don’t have: genuine, practitioner-level fluency in agentic development.
That decision — and everything that came out of it — makes my conversation with Chris a particularly fascinating one.
A framework that actually holds: the 3-bucket model for AI value creation.
Chris doesn’t talk about AI the way a lot of executives do. He comes in with a framework — one that’s clean, compelling, and consistent throughout.
Bucket 1: Agentic Development — Using AI to make product and engineering faster, better, and cheaper. This is the bucket accelerating fastest right now, and in Chris’s view, still in its infancy.
Bucket 2: Enterprise Operationalization — Making every function across the company more efficient — not just engineering, but ops, finance, support, and beyond.
Bucket 3: Net-New Product Capabilities — The things that simply weren’t possible before. New value delivered to customers that couldn’t have existed without AI.
Chris’s argument: most organizations are still dabbling at the edges of all three. They checked a box with a chatbot, deployed a copilot even. But they haven’t gone deep. That gap — the one between the checkbox and the real value — that’s where the opportunity lives.
What actually changes when you build with AI at scale.
Now at FastSpring, Chris is running the change management playbook in real time. Three things stand out from his experience in the trenches.
Context window management is the skill. Output degradation — and all the developer frustration it brings — isn’t just about model quality. It’s about what you feed the AI. Careful context window management really matters.
Vibe coding and agentic development are not the same thing. Vibe coding is fast and disposable: great for prototypes. Agentic development is deliberate: intentional architecture, upfront documentation, guardrails. Shipping something you can maintain, scale, and trust is a different discipline entirely.
Trust is earned incrementally. Like getting comfortable with Tesla’s full self-driving — you start skeptical, hovering over the wheel, until the technology earns enough confidence that you trust it more than your own instincts.
The sabbatical, the framework, the craft of building with AI at scale — the foundation, but not the whole story.
In the full episode, you’ll hear Chris’s thoughts on the human cost of this shift on engineering teams, why he believes one entire product role is already functionally dead, and what his own AI-powered personal operating system actually looks like running day-to-day.
We cover:
Why Chris thinks the engineers most at risk from AI aren’t the ones you’d expect — and which profile is about to have the best run of their career.
Building BunkOS: Chris’s own AI-powered Chief of Staff that knows his personality profiles, manages his calendar, and holds him accountable — and why he thinks the real barrier to building one isn’t technical ability, it’s the willingness to do it.
Why Chris, a self-described 98% believer in AGI happening in our lifetimes, recently caught himself wondering if it might already be here — and what specifically made him pause.
Chris, thank you.
This one stuck with me.
More About Chris: Chris Bunk is a technology executive with 20+ years of experience scaling teams and leading transformation in FinTech, SaaS, and PayTech. He has expertise in organizational design, AI-driven innovation, and full product lifecycle management. Chris has scaled engineering and product orgs from 15 to 200+ through to successful acquisition, driven 100% YoY growth in transactional volume and $2B+ in monthly transactions, and spearheaded organizational redesign for 300+ employees.
