Two Vermonters voted as top captive insurance professionals in the world

Sandy Bigglestone and Nancy Gray awarded top spots in recent industry awards.

Author: Vermont Captive

Montpelier, Vt. – The Captive Insurance Division of the Vermont Department of Financial Regulation (DFR) Deputy Commissioner of Captive Insurance Sandy Bigglestone, and Regional Managing Director – Americas for Aon Captive & Insurance Management Nancy Gray, were voted to top spots by their peers in Captive Review’s Power 50 Awards earlier this year. According to the Captive Review, over 7,800 captive insurance professionals around the world submitted their nominations and nominees were then judged on how they best met the criteria of influence, innovation, visibility/accessibility, skill/ability, and how dedicated they are to helping the broader industry.

Sandy Bigglestone portrait
                                 Sandy Bigglestone

Bigglestone, #3 on the Power 50 list, “is the major reason why Vermont has developed such a strong reputation and is on track to become the world’s largest captive domicile,” said Captive Review. “Now in the top job, her influence covers not just the captives the state regulates, but also other captive regulators, who often look to Vermont as the model of how to house and regulate captives.” 

In 2022, Bigglestone was promoted to Deputy Commissioner of the Captive Division, leading Vermont’s 30 captive insurance regulators. She spent the previous 13 years as Director of Captive Insurance and has worked for the Division since 1997.

“My relationship with the industry has been collaborative, supportive, and responsive.  It’s often rare that government and industry partner in this way,” said Bigglestone. “It’s important to me to employ the most reasonable regulatory standards for the industry, to be transparent about expectations, while at the same time, flexible to help the industry thrive.”

Michael Scott, VP & Associate General Counsel, Insurance for Farmers Business Network, has worked with both Bigglestone and Gray over the last 20 years in the regulation and management of their captive insurance company in Vermont.

“I’ve enjoyed working with Sandy and the State of Vermont because under Sandy’s time in the Division, it has become the gold standard of captive regulation,” said Scott. “The Division has always been the utmost professional, willing to discuss new ideas, and has helped captive owners’ structure unique programs while still maintaining the proper level of oversight.”

Captive Insurance Attorney Kathy Davis, who has been at the forefront of the captive industry in Vermont and the U.S. for over 30 years said, “Sandy has been a driver of innovation for the Vermont captive industry and her influence can be seen in captive insurance legislation and quality regulation not just in Vermont, but around the country and even around the world.” 

“Without a doubt the Division has the deepest bench of technical staff, leadership, and support from lawmakers compared to others around the country.  It’s the undisputed leader in the space with the most mature captive environment,” said Robert Moussaid, Director, Global Risk Management, Celanese, which also has a Vermont licensed captive insurance company. 

Nancy Gray portrait
                 Nancy Gray

Nancy Gray, #1 on the Power 50 list, was cited as a very popular figure with extensive influence. Nancy is responsible for Aon’s operations in the U.S., Bermuda, Cayman, Barbados, and Vancouver. With over 30 years of experience in the captive industry, she’s been part of Aon since 2001. In addition to her current Aon role, she has served as a director and past chair and treasurer of the National Risk Retention Association and serves as a director and officer for multiple captive clients. Previously, she served as a director and treasurer of the International Center for Captive Insurance Education and as a director and treasurer of the Vermont Captive Insurance Association. 

“I am a native Vermonter and proud of the reputation that the captive industry has developed in Vermont,” said Gray. “I was involved in the early days of the Vermont captive industry in the late 1980’s and early 1990’s as an auditor and then as a captive manager and pleased to have been part of the growth and development of the infrastructure.”  

“I’ve enjoyed working with Nancy over the years because she consistently took the time to understand my business needs and the needs of the captive,” said Scott. “She also consistently brought creative and strategic solutions to the table to help me meet those business needs. She is a problem-solver and is always available.” 

“From our initial contact, I was impressed by her professionalism and depth of knowledge and expertise in the captive space.  She became my ‘go to pro’ for all things captive,” said Moussaid. 

Gray recommends to anyone who wants to grow in the captive industry to actively participate in the industry, grow connections, and attend seminars and industry courses that are offered. “This is an industry that provides a lot of opportunity for career growth in an ever-changing environment that will continue to challenge you.” 

 Bigglestone adds, “My advice is to seek different perspectives from all concentrations in the industry and to never be shy to ask questions. I have enjoyed the fact that the industry provides an environment where there is always something to learn, and the industry itself exemplifies innovation.” 

Other notable mentions in this year’s Power 50 Awards include captive owners and Vermont-based service providers. About a third of the 20 captive owners listed had Vermont licensed captive insurance companies. Bob Gagliardi, a Vermont-based service provider of captive management company AIG was also listed. 


For more information on Vermont’s captive insurance industry, explore, call Brittany Nevins at 802-398-5192 or email 

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