For decades, CEOs have talked about scaling through systems, processes, and people. Now, there’s a new kind of employee in the mix that never sleeps, never complains, and learns faster than any human: AI.
My guest on The Scaling CEO, Sheldon Fernandez, has spent his career thinking about what that means for leaders. He’s the former CEO of Darwin AI, an AI company acquired by Apple, and now advises global enterprises on AI strategy, governance, and ethics. But Sheldon isn’t your typical technologist. He’s a computer engineer with a master’s degree in theology and philosophy. That mix makes him uniquely qualified to explore both the power and the responsibility of AI in business.
Philosophy Meets Technology
Sheldon describes himself as a “Renaissance man in an age of specialization.” That wide lens gave him the ability to make tough calls as CEO.
When his company took funding from Lockheed Martin, some academics on his team were uneasy. His training in ethics helped him build a framework for decision-making: where they’d draw lines, what values they’d defend, and how they’d operate responsibly.
For CEOs, the lesson is timeless: intellect without ethics is reckless. AI will amplify your principles or expose their absence.
Bias in Humans and Machines
AI bias gets plenty of attention. Sheldon argues that’s a good thing.
“One of the things we’ve learned is AI reveals things about our own human tendencies that we were blind to before.”
When his team released an open-source COVID detection model in 2020, they found it failed miserably when used on data from India and China. The problem wasn’t the algorithm—it was biased North American data. That discovery forced a deeper understanding of data quality, ethics, and humility.
For CEOs, the takeaway is clear: AI doesn’t just mirror our systems, it mirrors us.
Scaling Yourself Before Scaling Your Company
Before Darwin AI, Sheldon spent 16 years as a CTO. When the opportunity came to become CEO, he initially hesitated.
“It was one of those inflection points where you feel the holistic experience you have is set for the next journey.”
That shift taught him empathy for every role he’d once challenged. He now tells leaders that what makes you good at your current job can prevent you from becoming great at the next one. Scaling a company requires first scaling yourself.
AI Isn’t an Add-On, It’s a Rethink
Most CEOs see AI as a bolt-on productivity tool. Sheldon says that’s the wrong mindset.
“When AI is used in a transformative way, it’s not just a technological add-on. It necessitates reimagining the process itself.”
Like the early days of the internet, when publishers simply put magazines online, AI’s first wave will be about replication. The real revolution comes when CEOs use AI to reinvent how their companies operate.
Explainability: Why the Car Turned Left
Sheldon’s company once helped an autonomous vehicle client solve a bizarre problem: the car turned left more often when the sky was purple.
The reason? The training data came from Nevada sunsets.
That’s the danger of “black box” AI, unseen correlations that look statistically sound but make no sense in the real world. For CEOs in regulated industries, explainable AI (XAI) isn’t optional. You can’t manage what you don’t understand.
The Billion-Dollar Company With One Employee
In the latest State of AI Report, one prediction stood out: a billion-dollar unicorn with one employee. Sheldon sees the logic.
“The thing to scale now is going to be a machine, if you do it right.”
For CEOs, the question becomes: if you had a 24/7 analyst with PhD-level reasoning, what would they do for you? That’s the starting point for rethinking how AI fits into your organization.
Critical Thinking Now Happens in the Prompt
Sheldon believes AI shifts where thinking happens. It’s no longer in the task. It’s in the prompt.
“The critical thinking goes into how you set up the AI, how you lucidly write its instructions, and what you do with the output.”
In the future, CEOs won’t just need better analysts—they’ll need better writers. Clarity of thought translates directly into clarity of output.
Final Takeaway
Sheldon Fernandez reminds us that AI is no longer a tool. It’s a teammate. CEOs who embrace it thoughtfully will scale faster and smarter. But the same technology that magnifies capability also magnifies flaws. Ethical leadership, clarity, and curiosity will determine who thrives in this new era.
I’m Glenn Gow. I coach CEOs who want to scale with AI as their smartest employee. On my podcast, I reveal the strategies top leaders use to grow faster with ethics, structure, and vision.
Listen to the full episode of The Scaling CEO with Sheldon Fernandez for an unfiltered look at leadership, AI, and the future of scaling.
