The CTO Who Made Python a Personal Vendetta

When your entire career trained you to think one way, and AI demands the opposite.

Denise Hatzidakis started as a software developer. She has a degree in computer science, studied physics and electrical engineering, grew a company from startup to $2B across 10 states, and now serves as CTO and CPO at Borie Health. She’s been around code her entire career.

Which is exactly why AI threw her.

She enrolled in a Kaggle course that required building a RAG implementation in Python. Not because she couldn’t code — because AI demanded a completely different way of thinking than the one she’d spent 20 years sharpening.

“It was very fun, very challenging. It got to be a personal vendetta that I’m going to finish this whether I liked it or not.”

— Episode 39, The AI Product Leader

The unlearning problem

Here’s what Denise articulated better than anyone I’ve talked to on the podcast: the challenge for senior technical leaders isn’t learning AI. It’s unlearning the instincts that made them successful.

“You’re very conditioned to if-this-then-that and we’re not conditioned to explain what you want as the outcome.”

Twenty years of software development wires your brain for logic trees. Deterministic inputs, deterministic outputs. AI inverts that entirely. You describe a destination and let the model figure out the route. For someone with no programming background, that’s just how it works. For someone like Denise, it means fighting every instinct she’s built.

That’s what made it a vendetta. Not the Python syntax. The cognitive rewiring.

Why she did it anyway

Denise didn’t need to build a RAG implementation to keep her job. She’s a CTO. She could delegate every technical task and nobody would question it. Her reason for getting hands-on is the AI player-coach argument in its most precise form:

“I lead engineering teams and I think it’s important to be able to understand what they’re doing, what they’re talking about, what their challenges are — and help guide because it is different.”

That last phrase carries the weight: because it is different. AI isn’t another framework or platform her engineers are adopting. It requires a different mode of problem-solving. And a CTO who hasn’t personally felt that shift can’t guide a team through it.

Vetting the tools before the team does

When it came time to introduce Cursor to her engineering team, Denise personally vetted the privacy policies and data handling before approving it.

“We put in Cursor for our developers. And I said, ‘Okay guys, but we got to do this in a thoughtful process first.’ Let’s get the privacy — what do they say about what models do they use? Where’s our data going to go?”

In healthcare, where patient data and regulatory compliance raise the stakes on every tool decision, this matters. A CTO who has spent weeks wrestling with AI — who has felt the friction of prompting a model, evaluated its output, experienced how it handles context — reads a privacy policy with different eyes. She knows what questions to ask because she’s lived through the workflows herself.

The pattern

I’ve talked to over 60 senior leaders on the podcast now, and the ones making the sharpest decisions about AI share one trait: they’ve all been personally, recently humbled by it. They’ve sat with something that didn’t work. They’ve pushed through the discomfort of being a beginner at something adjacent to their expertise.

For Denise, the vendetta wasn’t about proving she could still write code. It was about rewiring how she thinks so she can lead a team through a shift that her own career hadn’t prepared her for. Her CS degree, her engineering background, her 20 years of building software — all of it was useful context. None of it was sufficient for AI.

She chose the discomfort of unlearning. Her team is better for it.

Polly Allen is the founder of AI Career Boost and host of The AI Product Leader podcast. She spent years leading AI at Amazon Alexa before building the AI Career Boost Blueprint, an 8-week program for Director+ product leaders becoming indispensable AI player-coaches. Subscribe to The AI Player-Coach newsletter →