Why AI Belongs In The First Mile Of A Purchase, Not The Last

Matt Wielbut is Co-Founder & Chief Technology Officer at Openly, a next-generation home insurance company.

Throughout industry circles, most insurance agents tell a version of the same story. A customer researches coverage online, compares quotes and maybe asks AI to explain policy language in plain English. They trade emails and texts with the agent about deductibles. Every step happens digitally by choice. Then, with the decision all but made, the customer asks, “Can you call me, or can I call you?” ​

That’s when customers want a real person—not an AI—to tell them they made the right call.

Online insurance shopping is nearly as old as the commercial internet, but independent agents still play a major role in the sale. They placed 39.5% of U.S. personal lines premium in 2025, their fifth straight annual gain, according to Big “I.” And even after the purchase, consumers still turn to people when they need help: In a 2026 Celent survey of auto insurance customers, 53% preferred a phone call with a live person for billing questions, while just 1% picked a chatbot.​

Every state requires a license to sell, solicit or negotiate insurance, under laws modeled on the NAIC’s Producer Licensing Model Act. An AI system can explain coverage without needing a license. Once it starts selling, soliciting or negotiating a specific policy, though, licensing comes into play.​

The NAIC’s AI model bulletin, adopted by 25 states and counting, requires insurers to govern their use of AI, including vendor tools. So if you’re automating anything in a licensed field, start with this: Whose license covers this step? Payment systems are asking the same question, and their answers reveal why insurance is harder.​

The Payment Rails Still Expect A Human

Nobody Wants The Liability

The Bottom Line​

Instead of automating the human out of the equation, my expectation is AI will continue to make agents more effective and customers more knowledgeable, which is better for everyone.​