From Strategy to Execution: How Alex Chimon Masters Every Discipline

Ever watch the show Money Heist on Netflix? The main character, nicknamed “El Professor,” reminds me a lot of Alex Chimon.

El Professor is a strategy mastermind with a plan for everything. He plans for success and for failure.

Alex is the same, except he’s not planning bank heists. He’s leading digital organizations.

He’s done it all—from running multi-million-dollar operations to rolling up his sleeves and digging into the messy world of healthcare technology, AI Robotics, and even co-founding a tequila company.

What Sets Alex Apart Is His Ability to Bridge the Gap Between Disciplines

Alex isn’t just a tech guy or a business strategist—he’s the full package, and that’s what makes him a leader who can actually get things done.

His experience reads like a “who’s who” of industry giants—Blue Cross Blue Shield, McDonald’s, HP—and he’s never been afraid to step into new arenas.

Digital transformation, healthcare chaos, AI, or scaling businesses?

Alex has handled it all, making him the guy you want in the room when the stakes are high. And today, he’s helping push the healthcare industry into the future, not by chasing the next flashy thing, but by getting the basics right and using AI to make real improvements where it matters.

I sat down with Alex to talk about healthcare, AI, and how he navigates a sector known for being notoriously slow to change.

‍Spoiler alert: it’s all about evolution, not transformation.

The Problem With “Transformation”

When I asked Alex what he thinks of the buzzword “digital transformation,” he didn’t hold back.

“It’s old,” he said, half-laughing. “If you’re still talking about digital transformation, you’re already behind. That ship has sailed. What healthcare needs is evolution, not transformation. You evolve to meet the challenges in front of you. If you’re still trying to ‘transform,’ you’re probably chasing problems that don’t exist anymore.”

It’s classic Alex—blunt but on point.

Healthcare has been digitally evolving for years. Organizations are no longer figuring out how to be digital; they’re struggling with how to make all these technologies work together.

Whether it’s electronic medical records (EMRs), telehealth platforms, or AI-driven patient care, the real task is getting them all to talk to each other. This requires an intelligent data layer, getting the systems to talk to each other, and having the right business processes in place.

“Too often, you see healthcare companies chasing technology for technology’s sake. They implement the latest system but forget about the bigger picture: improving patient outcomes and operational efficiency. If your shiny new tech doesn’t serve that goal, it’s just a distraction.”

From Patients to Payers: Who’s Really in Control?

Alex has this unique way of simplifying complex issues. Take the three main players in healthcare: patients, providers, and payors (insurance companies). They all have different demands, but in Alex’s mind, their needs aren’t that different.

“Patients want convenience—plain and simple. They want their data at their fingertips, their appointments seamless, and their care personalized. Providers, on the other hand, are struggling to keep up with tech they didn’t ask for and probably don’t love. And payors? They’ve got massive systems, thousands of integrations, and the impossible task of keeping all the plates spinning at once.”

For Alex, the key to improving healthcare is to find a way to make these three groups work in harmony. And that’s where technology, particularly AI, can make a real difference.

AI to the Rescue: Practical Applications Over Hype

You can feel Alex’s skepticism about AI hype from a mile away. But he’s quick to point out that when used correctly, AI is an absolute game-changer.

“AI isn’t some silver bullet. It’s a tool. And like any tool, it’s only as good as what you use it for. For healthcare, AI can do amazing things, like help doctors make better decisions, streamline claims for payors, and even help patients manage their own health better. But if it’s not solving a real problem, then what’s the point?”

Alex gives examples that show the practical side of AI: AI-driven adjudication systems that can process insurance claims faster and with fewer errors or AI-powered drug interaction warnings that can catch dangerous prescription combos before they harm patients.

“AI should be about improving patient outcomes first and foremost. If it’s not doing that, it’s just fancy software.”

Cutting Through the Noise: The Problem With Healthcare Systems

The biggest hurdle in healthcare, according to Alex, isn’t a lack of technology; it’s the systems themselves. Many healthcare organizations have antiquated systems, outdated solutions, and work with outdated or rigid business processes.

“Healthcare systems are like a giant game of telephone,” he says. “Everyone’s talking, but no one is hearing the same thing. Systems don’t integrate, data gets lost, and patients end up stuck in the middle.”

The solution? Integration. Not the sexiest word in tech, but Alex insists it’s the one that will make all the difference.

When systems can seamlessly share data, AI can step in and do its job—whether that’s personalizing treatment plans or catching errors in billing.

Innovation, But at What Cost?

So, what’s the catch? Cost. Healthcare isn’t known for its deep pockets, despite what people might think. Even organizations with massive budgets are cautious about where they spend it.

“There’s this perception that healthcare is rolling in cash, but that’s not true. They have money, sure, but it’s allocated to a thousand different things. When they do spend on tech, they want to know it’s going to pay off. AI has to deliver real value, whether that’s saving money, reducing errors, or improving patient outcomes.”

It’s clear that, for Alex, the ROI on AI isn’t just about financial savings—it’s about making the whole system work better for everyone involved.

The Future of Healthcare: Evolution Over Revolution

As we wrapped up, I asked Alex where he sees the future of healthcare heading. His answer was as pragmatic as ever.

“We’re not going to see a revolution. Healthcare doesn’t work like that. What we’re going to see is incremental, practical changes that lead to real improvements. AI will play a big role, but only if it’s used to solve actual problems, not just because it’s the latest trend.”

So, what’s the takeaway? For Alex Chimon, it’s simple: evolve or get left behind. Healthcare might be slow to move, but with leaders like Alex pushing for smart, strategic use of AI, the industry might just catch up.

And if you’re still talking about “transformation”? Well, according to Alex, you’re already too late.

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