When Jason Wells talks about artificial intelligence, he rarely starts with technology. In our conversation, he leaned back and said simply, “Forget AI for a minute. Just tell me about your business. What are the issues? Where do you wish you could be more efficient?” The line captures his habit of cutting through hype to focus on what leaders actually face day to day.
Wells’ career spans Sony Pictures to startups, but the pattern is consistent: massive, billion-dollar initiatives that collapse under their own weight, contrasted with the small, practical wins that build momentum. “I have seen what happens when companies go too big too fast,” he told me, recalling a project that spent two years and a billion dollars before being scrapped entirely. That lesson shaped his insistence on bite-sized steps.
Outside the boardroom, Wells is a four-time Ironman finisher, a detail he mentions almost in passing, but one that signals the endurance he brings to leadership. It also explains why he is so patient with executives who feel paralyzed by the mix of AI hype and the memory of past failures.
As Wells puts it, leaders get stuck “between two forces:” the promise that every tool looks magical at first, and the fear of wasting millions when it isn’t. That tension, he says, is why his work begins not with technology but with business fundamentals. It is also the reason our first question was how he helps CEOs and founders move past the noise and focus on what really matters for their business.
Q&A With Jason Wells
Q
Many executives feel uncertain about where to even begin with AI. What do you see as the biggest roadblocks leaders face when they start exploring it?
A
Jason Wells: I tend to start by understanding where their pain points are when it comes to AI, what they are worried about, what their concerns are, and what they think can work. Everybody has a moment of not knowing what AI really is, and then they will say something that shows me where the soft spots are. I often tell them to forget AI for a minute. Just tell me about your business. What are the issues? Where do you wish you could be more efficient?
What I find is that leaders get caught between two forces. On one side is the AI hype, where every tool looks magical at first. On the other side is the memory of big, failed projects that burned money and trust. That combination of noise and fear keeps people from taking the first step. My role is to help them see where the opportunity is real and where it is not, so their first step is a solid one.
Q
When you sit down with a CEO or founder for the first time, how do you help them cut through the noise and focus on what really matters for their business?
A
Jason Wells: A lot of people come in saying they want AI to do something specific for them, like in one case, to answer the phones in a call center. This CEO with a 17-person call center I worked with was convinced AI could take over. On the surface that looks simple, but when we dug in, we found that a small nuance in a mapping API created complications that took us two weeks to uncover. That is the reality beneath all the excitement.
So my first move is to understand the business model. How does the company make money? What are the bottlenecks? Once I know that, I can educate them on what is possible and what is not. That turns the conversation from shiny tools into strategy. Instead of chasing magic, we focus on the specific areas where AI can give them a real, measurable lift.
Q
You often stress the importance of small, practical wins over massive projects. Why do you think that approach resonates so strongly with executives?
A
Jason Wells: I have seen what happens when companies go too big too fast. Early in my career, I was part of a project where the company spent two years and a billion dollars trying to launch new technology. I joined in the final eight months, and every week 20 people on conference calls debating next steps. In the end, leadership announced they were pulling the plug and writing it off completely. A billion dollars gone, just like that. That is the absolute wrong way to go about things.
Executives resonate with small wins because they avoid that kind of risk. They are not betting everything on one massive project. Instead, they are learning as they go, getting value right away, and building trust step by step. You should always have a big vision, but the way to get there is through bite-size steps that prove value along the way. Each quick win shows the team that AI can actually work for their business, and that momentum is what builds confidence and lasting transformation.
Q
Can you share an example of how a quick win has created momentum for bigger change inside a company?
A
Jason Wells: At NOW CFO, it started with just a project, but soon I was pulled into executive team meetings because they were worried about why sales were dropping. I took a week, pulled out the numbers, running analytics on every sales conversation, and came back with an insight that changed everything. We found that 80 percent of clients closed within 10 days of the first call, and after that it dropped off sharply. That discovery completely reshaped how they approached their sales process.
From there, we built a tool that used natural language processing to analyze sales conversations going forward. What began as a small analysis became the foundation for bigger strategy discussions. That is the power of a quick win. It earns trust and opens the door to transformation.
Q
There’s a lot of pressure on leaders to move fast with AI, but also a lot of fear around wasted investment. How do you strike the right balance between caution and action?
A
Jason Wells: I think the balance comes from how you take responsibility. Early in my career as a management consultant, the model was to hand over a deck and walk away. That is not enough anymore. Leaders today want someone who will share responsibility for adoption and make sure it actually delivers results. That is why I sometimes take an operational approach, where I literally take over a specific pain point, design the automation pipeline, and build the automation behind the scenes using machine learning models and workflow integrations. Then I deliver the result as if they had paid for the custom solution all along.
That way the company does not carry the risk of a massive AI initiative. They get measurable value, they see what is possible, and they do not have to worry about all the messy adoption steps. It moves fast, but stays controlled. They get progress without the billion-dollar mistakes.
“What I find is that leaders get caught between two forces. On one side is the AI hype, where every tool looks magical at first. On the other side is the memory of big, failed projects that burned money and trust. That combination of noise and fear keeps people from taking the first step.”
Q
From your perspective, what does it take for an executive team to successfully integrate AI into the broader strategy of the business?
A
Jason Wells: Rarely is it just “can you build this for me?” The companies that get the most impact are the ones that bring me into the bigger conversation from the start. For example, a paratransit company I worked with began AI automation, but before long, the CEO asked me to join his sales strategy sessions and tell him how to expand the business. That is where the real value comes from.
It takes willingness to let AI become part of the C-suite dialogue. When that happens, the emphasis shifts from isolated tools to strategic outcomes such as growth, efficiency, and competitive positioning. AI becomes part of the leadership toolkit, not the only thing. That integration is what makes it stick.
Q
Looking ahead, how do you see the role of AI evolving in the C-suite, and what advice would you give to leaders who want to stay ahead of that shift?
A
Jason Wells: The role of AI in the C-suite is already moving past being just a tool. In many cases, I work as a member of the executive team, where AI is only part of the conversation. From there it shifts into sales, operations, and long-term growth. That shows how fully AI is becoming part of how decisions are made.
For leaders who want to stay ahead, the advice is not to chase the flash. I have been working on AI video generation, and the demos online look amazing; but reproducing them in real business is far more complex than people realize. Almost everything you see takes more time, more work, and more resources than it appears. The real differentiator is not the technology itself anymore. It’s knowing how to take small, smart steps that move the business forward. That is what keeps leaders ahead of the curve.
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About Jason Wells
Jason Wells is the Founder of AI Dev Lab and a Fractional Chief AI Officer. He has led global teams as Senior Vice President of Digital Media Worldwide at Sony Pictures, served as CEO of Convirza, and most recently as Chief AI Officer at NOW CFO. Jason partners with leaders to turn AI into an advantage, using practical strategies that drive efficiency and lasting transformation. A four-time Ironman finisher, he brings resilience, clarity, and a global perspective to technology and leadership.
