''' I’m going to say something that might get me in trouble. The hottest new role in the C-suite, the Chief AI Officer, is a complete waste of money for 9 out of 10 companies.
I’ve seen it dozens of times in the last year. A board gets nervous, they read some headlines, and suddenly the CEO has a mandate: "We need an AI strategy!" The fastest way to check that box? Hire a Chief AI Officer. It looks decisive. It feels like progress. But it’s usually just a smokescreen.
The Symptom, Not the Cure
Hiring a CAIO is often a symptom of a much deeper problem: a fundamental lack of understanding of what AI is and how it should integrate into the business. Companies are treating AI like it’s a separate, mystical department you can bolt onto the side of the existing org chart. It’s not. That’s like hiring a "Chief Electricity Officer" in the 1920s.
When I was scaling my first company, RemoteTeam, we didn’t have a "Chief Internet Officer." We all had to become internet-literate. The same is true for AI. It’s a horizontal transformation, not a vertical one. It touches every part of the business—product, marketing, operations, finance. Isolating it under one executive, who often has a limited budget and even less real authority, is a recipe for failure.
This person gets a fancy title, spends six months creating a beautiful "AI strategy" deck, and then what? They have to beg and borrow engineers from other teams. They have to fight for budget against established product roadmaps. The rest of the executive team breathes a sigh of relief, thinking "Good, AI is handled," and goes back to business as usual. The CAIO becomes an island, and the strategy deck gathers dust.
My "Aha!" Moment with an AI Investment
I remember talking to the founder of an early-stage AI company I invested in. They were building incredible tech, but struggling to get traction. Their potential customers were all big enterprises, and they kept getting stuck in meetings with the brand new Chief AI Officer.
The founder told me, "It’s a black hole. The CAIO loves our tech, but they can’t actually buy anything. They have to get buy-in from the Head of Product, the CTO, and the business unit leader. By the time they coordinate all of that, the budget is gone or the priorities have changed."
That was a huge "aha!" moment for me. The CAIO was a bottleneck, not an enabler. The companies that were actually making progress were the ones where the CEO, the CTO, and the product leaders were all deeply engaged in the AI strategy themselves.
What to Do Instead: A Practical Guide
So if hiring a CAIO is a mistake, what’s the right move? It’s harder, but it’s also far more effective.
1. Education Starts at the Top: Your entire leadership team needs to become AI-literate. I’m not saying they need to code neural networks. But they need to understand the difference between generative AI and predictive AI. They need to know what a large language model is and what it’s good at. They need to have a real intuition for what’s possible and what’s hype. I run workshops for the leadership teams of my portfolio companies on exactly this. It’s non-negotiable.
2. Empower Your Product and Tech Leaders: The people who are closest to the product and the technology should be the ones driving the AI initiatives. Your CTO should be your chief technologist, and that includes AI. Your Head of Product should be obsessed with how AI can create better user experiences. Give them the mandate and the resources. Don’t create a new C-level executive to compete with them.
3. Start Small and Get Wins on the Board: Instead of a grandiose, top-down AI strategy, focus on specific, high-impact use cases. Find a real business problem and solve it with AI. At MovieLaLa, we didn’t set out to "do AI." We wanted to give better movie recommendations than anyone else. That led us down the path of machine learning, and we built our expertise from there. The momentum from a real win is a thousand times more powerful than any strategy deck.
4. Hire for AI Skills Across the Board: Instead of concentrating all your AI talent in one department, embed it in every team. Your marketing team should have someone who knows how to use AI for customer segmentation. Your finance team should have someone who can build predictive models. AI is a skill, not a department.
The One Time a CAIO Makes Sense
Is there ever a time to hire a CAIO? Yes, but it’s rare. If you’re a massive, multinational conglomerate with dozens of disconnected business units, a CAIO can sometimes act as a central coordinator and evangelist. But even then, their primary job should be to make themselves obsolete by building AI competency within each business unit.
For everyone else—for the 90% of companies that are just trying to figure out how to compete in this new era—the CAIO is a distraction. It’s a comforting illusion of progress. Don’t fall for it. The real work is harder, but it’s the only way to actually win.
Stop looking for a savior. Roll up your sleeves and get your hands dirty. The AI transformation won’t be led by a single executive. It will be led by the companies where everyone, from the CEO down, is part of the revolution. ''')) HBox(children=(FloatProgress(value=0.0, max=1.0), HTML(value=
Frequently Asked Questions
Do all experts agree with this view?
No, and that's fine. The best ideas in business are often contrarian. I share my perspective based on my experience and data, but I encourage you to seek out opposing viewpoints and form your own conclusions.
What experience informs this perspective?
This perspective comes from over a decade of building companies in Silicon Valley, two successful exits (RemoteTeam to Gusto, MovieLaLa to Gfycat), and investing in 200+ startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.
How has this view evolved over time?
My thinking on most topics has changed significantly over the years. Early in my career, I held many conventional views that experience proved wrong. I try to update my beliefs when the evidence changes.