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.

CAIOs don’t want to be left out of strategy conversations.—BH

Do you want the bad news or the bad news?

Amid a 121-page report exploring more than 31,000 cyber incidents and attack trends over the course of a year (including mobile-centric social engineering, shadow AI, ransomware, and more), Verizon’s annual Data Breach Investigations Report (DBIR) also revealed a growing mismatch for the IT pro: Along with a rise in vulnerability exploits, there are more patches than a cybersecurity team can realistically implement.

“Put quite simply, there are often too many vulnerabilities and not enough time for patching all of them,” the report’s authors wrote in their study, published on May 19.

What’s the median number of days it took IT pros to patch a KEV?—BH

New employment data for the tech sector shows the impact of AI on hiring.

Numbers from tech certification provider CompTIA, working off data from the Bureau of Labor Statistics, show that AI hiring intent—job listings for specialized AI roles or that require a specific AI skill—has doubled since November 2025. It’s a sign both of the continued strength of tech sector employment and the importance of AI to the industry.

Seth Robinson, CompTIA VP of industry research, told IT Brew that the scale of the increase is even greater than the current intent indicates. CompTIA’s tracking of AI jobs already started at a high baseline in May 2024.

Many skills defined as AI-related—such as machine learning and automation management—predate the current boom, which began with the introduction of generative AI models like ChatGPT at the end of 2022.

And there’s no sign of slowing down either.—EH

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