Two Vermonters named among world's top captive insurance professionals

Nancy Gray, regional managing director for the Americas of Aon's captive and insurance management practice, and Sandy Bigglestone, deputy commissioner of the captive insurance division at the Vermont Department of Financial Regulation, were voted to the first and third spots, respectively, of Captive Review's Power 50 rankings earlier this year. Captive Review is the leading source of news and analysis for the risk management and captive insurance communities.

Gray, who oversees Aon's operations in the US, Bermuda, Cayman, Barbados and Vancouver, was recognized by her peers as a popular figure with extensive influence. In addition to her management responsibilities, she acts as a senior adviser to several large captives and assists new clients in evaluating and implementing captive programs.

“I am a native Vermonter and proud of the reputation that the captive industry has developed in Vermont,” Gray said.

Bigglestone, who leads Vermont's 30 captive insurance regulators, “is the major reason why Vermont has developed such a strong reputation and is on track to become the world’s largest captive domicile,” the Captive Review said.

Prior to being promoted to her current position in 2022, Bigglestone spent the previous 13 years as director of captive insurance. She has worked for the Division of Captive Insurance since 1997.

“My relationship with the industry has been collaborative, supportive and responsive,” she said. “It’s important to me to employ the most reasonable regulatory standards for the industry and be transparent about expectations while at the same time flexible to help the industry thrive.”