I’m going to say something that might get me in trouble. Hiring a Chief AI Officer is one of the biggest mistakes I see companies making right now. It’s a solution in search of a problem, and it’s a giant red flag that tells me a company doesn’t truly understand what it takes to integrate artificial intelligence into its business.
I’ve seen this movie before. A new technology comes along, and suddenly every company is scrambling to hire a “Chief” of that new thing. It happened with social media, it happened with mobile, and now it’s happening with AI. But here’s the hard truth: AI isn’t a new department. It’s a new way of working. It’s a horizontal layer that should touch every single part of your organization, from product and engineering to marketing and sales. When you hire a CAIO, you’re siloing AI. You’re turning it into a cost center, a bottleneck, and a single point of failure.
My Own Experiences Tell Me This is a Bad Idea
When we were building RemoteTeam, we didn’t have a “Chief of Remote Work.” We were all chiefs of remote work. It was in our DNA. We had to be, to survive and then to thrive. We built a culture where everyone was empowered to think about how to make remote work better. The same was true at MovieLaLa. We didn’t have a “Chief of Mobile.” We had a team of passionate people who were obsessed with building the best mobile experience for movie lovers. We didn’t need a chief to tell us that mobile was important. We just knew.
I’ve also been fortunate to invest in over 200 companies, including some of the most important AI companies in the world like Anthropic, OpenAI, Scale AI, and Hugging Face. I can tell you that none of them have a Chief AI Officer. Why? Because AI is their business. It’s not a department. It’s not a silo. It’s the very fabric of their company.
The Real Problem with the CAIO Role
The problem with the CAIO role is that it’s a symptom of a much deeper issue: a lack of leadership and a fear of the unknown. Companies that hire CAIOs are often the ones where the CEO, the CTO, and the rest of the executive team don’t understand AI. They’re hoping that they can just hire someone to “handle it” for them. But that’s not how it works. You can’t delegate the future of your company.
The best AI talent doesn’t want to work for a CAIO. They want to work on the front lines, solving real problems. They want to be embedded in product teams, working alongside engineers and designers to build the next generation of intelligent products. They don’t want to be stuck in a corporate ivory tower, writing strategy documents that no one will ever read.
What You Should Be Doing Instead
So, if hiring a CAIO is a mistake, what should you be doing instead? Here are a few things that I’ve seen work:
Educate your existing leadership. Your CEO, your CTO, and your entire executive team need to understand AI. They don’t need to be experts, but they need to understand the fundamentals. They need to be able to have an intelligent conversation about how AI can be used to create value for your customers and your business. I wrote my book, "Becoming Top 1%", for this very reason - to help leaders understand how to think about and leverage technology.
Empower your teams. Create a culture of experimentation and innovation. Give your engineers and product managers the tools and the autonomy to play with AI. Encourage them to come up with new ideas and to build prototypes. Some of the best ideas will come from the bottom up, not the top down.
Hire AI talent into existing teams. Don’t create a separate AI team. Instead, hire AI experts and embed them in your product, marketing, and engineering teams. This will ensure that AI is being used to solve real problems and that it’s being integrated into your products and services from the very beginning.
The Bottom Line
Look, I get it. AI is moving fast, and it can be scary. It’s tempting to think that you can just hire a CAIO and all your problems will be solved. But that’s a fantasy. The truth is that there are no shortcuts. You have to do the hard work of building a culture of innovation, educating your leadership, and empowering your teams.
Don’t waste your money on a Chief AI Officer. Invest it in your people. Invest it in your culture. And most importantly, invest it in your own education. The future of your company depends on it.
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.
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.
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.
What's the most common pushback you get on this?
People often push back by citing exceptions or edge cases. And they're usually right that exceptions exist. But building a strategy around exceptions rather than patterns is a losing game for most founders.