Artificial intelligence technology has continued to evolve, and it’s affecting many areas of insurance from claims to underwriting to customer service, according to panelists at the 2025 PLUS D&O Symposium in New York City.

But has the technology developed so much that it could replace human underwriting in the next five years?

“I think it is the biggest question out there,” said Jeffrey Chivers, CEO and co-founder of Syllo, an AI-powered litigation workspace that enables lawyers and paralegals to use language models throughout the litigation life cycle.

Another way of asking this question is whether AI can develop judgment, not just in underwriting but across all business domains in which judgment is an essential part of the job, he said.

“Is there any change here with respect to a model’s ability to exercise the kind of nuanced value judgment and other types of judgments that go into a mission critical job?” he asked. “Thus far, the answer for me has been no,” he said. “If the answer is yes at some time in the next five years, I think t

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