Award-winning CIO Jason James believes leadership isn’t about choosing between technology and humanity. It’s about holding both.
Jason James has spent more than 25 years in technology, and these days he’s managing artificial intelligence, cybersecurity, cloud infrastructure, and enterprise transformation as an award-winning CIO. On paper, that makes him a technologist through and through.
Sit with him for an hour, though, and the tech barely comes up. He’s relaxed, quick with a joke, the kind of guy who’d rather talk about barbecue than bandwidth. More than once I had to remind myself to steer us back to CIO territory instead of chasing him down another rabbit hole on movies, music, or food. But what he kept circling back to, again and again, was people.
“When I’m on my deathbed, nobody’s gonna remember any of it,” Jason told me, describing the technology he has built and managed throughout his career. “They’re gonna remember what I did for their career. They’re gonna remember the opportunities, the mentoring.”
That instinct opens his forthcoming book, Make IT Work: An IT Playbook for Mergers and Acquisitions which starts with three words: “Leaders create leaders.”
For Jason, holding speed and patience at the same time, moving fast without losing sight of the people around him, is the job itself. Plenty of leaders lose that balance, perhaps without meaning to. They get caught up in pressure to move fast, chase the next initiative, or keep everyone happy. Sometimes it’s a blind spot. Sometimes they just don’t know how to push back against that pressure. Jason does, and you can hear it in the specifics: he tells his team to be realistic about deadlines, then just as quickly tells them not to burn themselves out. He questions the market’s rush to cut costs wherever it looks cheapest, without asking what gets lost along with it. The goal is to move fast enough to matter and slow enough to develop his people.
Earn the Right to Change Things
Jason doesn’t fit the traditional image of a CIO. He’s more likely to show up in bright sneakers than a tie, and his book carries plenty of humor, pop culture references, and a running joke about barbecue that surfaces eleven times.
The bigger departure is philosophical. Jason believes a CIO should help shape where the business is headed, not just execute what other departments hand down.
“If you’re looking for a transformational CIO, I’m it,” he said. “But if you’re looking for somebody to take your order, why don’t you go get fast food?” He said it without missing a beat, like a line he’s used before and still enjoys.
Earning the room to push back on conventional thinking takes more than good ideas, though. When I asked him how he’d built that kind of trust, his answer was about the ability to deliver.
“You have to deliver,” he said. “It doesn’t matter how great your ideas are. It doesn’t matter how well thought they are. If you can’t keep the lights on, nobody’s gonna trust you to do anything transformative.”
That’s the balance running through his whole approach. A leader who spends every hour protecting today’s operation never gets around to building tomorrow’s organization. A leader chasing tomorrow while ignoring today’s responsibilities never earns the credibility to get there. Transformation doesn’t replace execution. It raises the bar for both.
“In order to be given more,” Jason said, “you gotta deliver on what you have been given.”
Knowing People Well Enough to Push Them
Jason has worked his way through nearly every role he now oversees, which gives him what he calls an “acute BS meter.” He knows when a task should take two hours, and he knows when someone is quietly being asked to compress two days of work into a few hours.
That combination produces an unusual mix of accountability and empathy. Jason pushes his team hard because he understands their work well enough to know what’s reasonable, and that same understanding keeps him from pushing past the point of burnout.
It’s paid off in a way most executives would envy. Jason said his teams have had the lowest attrition rates at each of his last three companies. His explanation is simple.
“People are more than their positions,” he said. “You gotta know them as a person. You’ve gotta ask them what they want. You’ve gotta figure out what motivates them.”
That doesn’t mean shaping everyone into his own image. Some people want his job someday, but plenty don’t.
“I don’t want them to be me,” Jason said. “I want them to be them.”
When AI Makes Everyone Busier
Artificial intelligence is supposed to free up time by automating repetitive work and speeding up decisions. Yet Jason sees plenty of people who feel busier than ever, not less.
Part of the reason, he thinks, has nothing to do with AI. “We live in noise,” he said. Constant news, phones, notifications, and competing demands keep people’s nerves heightened around the clock.
“We need to learn to quiet our minds. We need to learn to disconnect,” he said. Then he added a line that’s easy to miss coming from someone whose job is built around deploying more technology: “Tech’s not gonna fix everything.”
That applies inside organizations just as much as it does to individuals. “If I’ve got broken processes, tech just makes them break faster,” Jason said. AI can speed up a process without making it better, increase output without improving outcomes, and hand employees more capability without telling them what to do with it. The real question companies need to ask isn’t how fast AI lets them move. It’s whether they should be moving that direction at all.
Potential and Peril in Equal Measure
Jason sums up the current moment in enterprise AI with three words: “Potential, peril, and promise.” Companies are already seeing real gains in areas like quality assurance, technical writing, and cybersecurity, and he expects those gains to grow as AI moves past pilot programs into everyday operations.
But he’s also candid about how early this still is, and how expensive early can get. He compares the current corporate AI race to the Manhattan Project, with every organization running its own version at once. Eventually, though, the spending has to be justified.
“You have to justify the cost,” he said.
Jason recently came across an enterprise AI license running about $4,000 a month for a technical writing use case. His reaction was blunt: “At that price you could just hire an MFA student.” The joke carries a real business question underneath it. Jason isn’t arguing against investing in AI. He’s arguing for spending it with judgment.
Protecting the Pipeline
That same judgment shapes how Jason thinks about entry-level jobs, which some companies are already reconsidering as AI takes over tasks once handled by junior employees. He sees a contradiction in that thinking. Organizations talk constantly about building leadership pipelines, then consider eliminating the bottom rung of the ladder that feeds them.
“We can get rid of all of our young developers,” he said, describing the reasoning he hears in parts of the market these days: AI can now handle a good chunk of what junior developers used to do, so why keep paying for the entry-level headcount. It’s the kind of thinking that looks smart on a spreadsheet and shortsighted everywhere else, and it’s exactly the kind of tradeoff that sets him off. Jason’s response is far less enthusiastic: “What the hell are you doing?”
Cutting junior roles doesn’t just remove a line item from a budget. It can remove the environment where future senior leadrs learn their craft. Jason also points out a flaw in the math: if cost reduction is the real goal, why start with some of the least expensive people in the building?
Judgment Becomes the Advantage
Jason can rattle off what’s coming next without missing a beat: Amazon deploying 300,000 humanoid robots on factory floors, coal mines once too dangerous for humans reopening with robots doing the work, elder care robots that could let people stay in their own homes years longer than a nursing facility would. On the cybersecurity side, he points to nation-states that have quietly been stealing encrypted data for years, betting that quantum computing will eventually hand them the key to unlock it. But you can’t miss his enthusiasm for what’s possible, either.
He asked if I’d seen the Avengers movies. I have two boys, so naturally I’ve seen them more than a few times. But Jason pointed out a line I’d never really considered. Back in 2018, he wrote an article asking, half-joking, whether AI was our Thanos. He likes to riff on the line “dread it, run from it, destiny still arrives,” then flip the ending: it’s here now, whether we’re ready or not. Then he pivots straight to the upside. AI is already helping doctors catch cancer years earlier than traditional screening allows, which is exactly the kind of destiny he’s willing to run toward.
I asked him where he thought we’d all be in five years, once we could look back on this stretch with some distance. Part of his optimism about that comes from his own family history. He grew up a few hours south of Atlanta, in a family with deep roots in Alabama’s cotton mills, and he watched those jobs disappear as manufacturing moved overseas. He remembers his father asking a simple question when a family member was hoping someone would buy and reopen a shuttered plant: “What is your plan if that doesn’t happen?”
That question shaped how Jason thinks about careers today. Two centuries ago, most American workers farmed for a living. Now only a small fraction do, and the jobs that replaced agriculture didn’t exist yet for anyone to predict. Jason expects AI to trigger a similar shift, and he thinks it favors skills that are distinctly human.
“I’m very hopeful that the rise of the humanities will come again,” he said. AI is making information nearly universal, which means the ability to interpret it, question it, and put it in context becomes more valuable, not less.
Small Markets, Real People
Jason also sees AI lowering the cost of turning an idea into something real. A person who once needed a full development team can now describe what they want and have AI build much of it, a shift he calls “the rise of the citizen developer.” That opens up markets that never made financial sense before: small, passionate communities too niche to justify a traditional app or platform. Jason points to his own hobbies as the kind of audience someone could now build for, like tiki culture, the vintage tropical-bar scene built around rum cocktails and collectible carved mugs, and competition barbecue.
At the same time, he’s noticed people placing more value on things that feel distinctly human as digital creation gets cheaper. He recently took his daughter to Perimeter Mall and was surprised by how crowded it was with young people. He jokingly called them “modern Luddites,” pushing back against the digital world built for them.
“They built all this technology BS for us. I’m gonna go live life,” he said, describing their attitude. His response: “Bravo.”
Planting Trees for Shade He Won’t Sit In
When I asked Jason what motivates him as he thinks about the future, his answer was immediate: “My children. And my children’s children.” He opened college savings accounts for his kids years before he’d even met his wife, a small detail that says a lot about how far out he plans.
He referenced an old proverb toward the end of our conversation. The best time to plant a tree was 20 years ago. The second-best time is today. The value of the tree isn’t for the person who plants it. It’s for whoever needs the shade later.
That’s the thread running through everything Jason does, from how he manages his team to how he thinks about AI investment. Move fast enough to stay relevant, and slow down enough to think. Automate what machines should handle, and develop what only humans can become. Demand performance today, and protect the people building tomorrow.
“Leaders create leaders,” Jason said. In an era when technology promises to make almost everything faster, that might be the one thing worth taking slow.
