How today’s CAIOs deal with the pressure to transform

Daniel Herrington is still getting the hang of being a chief AI officer.

He’s in his fifth month as CAIO at The Zebra, a marketplace for home and auto insurance. “I think my role is to put hands on the keyboard, and build, and inspire the rest of the team to engage with new technologies and understand them,” he said.

That involves experimenting with what AI can do. Most recently, Herrington tested a chatbot’s ability to surface a policy option—by analyzing an LLM’s responses against thousands of synthetic conversations.

But there’s a pressure on CAIOs to prove that their AI is transformative and moving (quickly) beyond just a successful pilot. A recent Deloitte study of over 1,800 execs across Europe and the Middle East found that:

• More than 9 of 10 respondents plan to increase AI investment in 2026.
• 62% said they see satisfactory ROI on a typical AI use case within two to four years—significantly longer than the seven-to-12-month average payback time for a tech investment.

Cloud cost optimization platform CloudZero recently estimated that a built-from-scratch custom AI project “of mid-complexity” would cost anywhere from $40,000 to $250,000 (with monthly API and compute costs spanning $500 to over $50,000).

We spoke with CAIOs about their strategies for handling the transformative pressures of the role.

Pro CAIO! An IBM survey of 2,000 global CEOs found that more than 3 in 4 respondents (76%) reported having a chief AI officer in 2026—up from 26% in 2025.

In the same report, IBM positioned the role as “critical” and advised organizations to give a CAIO “authority over AI priorities, standards, and funding gates—but not ownership of business results.”

“Line leaders remain accountable for outcomes. That separation is what enables speed without chaos,” the report authors wrote.

Whoa, whoa, CAIO. Sebastian Wernicke, partner at finance and economic consultancy Oxera, sees companies sometimes putting the CAIO in a bit of a trap: They are defined as the leaders introducing AI technology, and judged on how effectively the AI transforms business processes—yet they’re often left out of the strategy conversation.

“If you frame it as a purely technical and IT function, I think you cannot change how a company makes their decisions from inside IT,” Wernicke said. “You need to be in the room where strategy is happening, and where the operational part of the business is taking place, and so unless you actually align these expectations with the setup, which I think oftentimes, unfortunately, is not the case, then you’re setting yourself up for disappointment.”

Dissatisfaction can seep into the business, he added, when the company has made significant AI investments but only achieved “incremental steps” rather than sweeping transformation.

An AI executive with influence on technology investment, data management, and governance may also have responsibilities that overlap with other tech officer roles like CIO and CTO, leaving some to debate if the role has an expiration date.

Getting to work. Herrington says he tries to collaborate rather than collide with other tech leaders in the business.

Before his interview with IT Brew, he was erasing a whiteboard with the results of a data-paradigm jam session with the company’s VP of data. The current vibes are democratic, he said: “We come up with a solution together and bring it to the team. Maybe that will collide one day, but right now it’s been true collaboration.”

He spoke of already bouncing ideas off the CTO (who decides platforms and models, he said), discussing risk posture with the security team, and talking intellectual property with legal.

One of Herrington’s first tasks involved the deployment of GenAI to merge disparate carrier questionnaires and allow customers to answer multiple sets of questions at once. A former senior product manager at Google, he sees the benefits in thinking ahead and adopting his former employer’s philosophy of “NBU,” or building for the “next billion users.”

“I’m not looking for the things that move the business by 1 percent. That’s not a place where I can invest my time if I’m going to be successful in this role,” he said.

Transformation permutations. To a CAIO, transformation can begin with a big idea or slow cultural shift.

Kendrick Kho is also a new CAIO, just a few months into his tenure at financial professional services firm Scrubbed. He’s currently selecting enterprise AI tools and trying to train and inspire “citizen developers.”

“They can be the ones actually defining the business process transformation,” he said, “because I don’t come from an accounting world, a tax world.”

In a similar vein, Herrington recently hosted a “vibe-athon” (a common occurrence these days), where an advisor manager built a training tool from existing customer transcripts. Whether or not that kind of AI transformation, which encourages everyone to put hands on a keyboard, helps or hurts job security, he appreciates how he’s helping his organization embrace the technology: “The key thing there was our advisors learned that they could build tools for themselves.”