Governor Phil Scott appoints Sandy Bigglestone to lead captive industry

Vermont looks within for most qualified leader

Author: Vermont Captive

Montpelier, Vt. – Governor Phil Scott has appointed Sandy Bigglestone to become the Deputy Commissioner of the Captive Insurance Division at the Department of Financial Regulation (DFR) at the end of the summer, ensuring a smooth transition in the role from current Deputy Commissioner David Provost, who is retiring. Bigglestone is currently the Director of Captive Insurance.

“Sandy has decades of experience in licensing and regulating captives in Vermont, the top domicile in the country. It made sense to look within for the best person to lead the industry and the obvious choice was Sandy. I look forward to all she will do moving forward in support of this great industry,” said Governor Phil Scott.

Bigglestone started as an entry-level examiner in the Captive Insurance Division in 1997, promoted to Director of Examinations in 2008, and then named Director of Captive Insurance in 2010, a role which manages the Division’s operations and oversight of the licensing and monitoring of Vermont’s captive insurance companies.

“I’ve worked with Sandy for over 20 years – I’m confident that she’ll carry on the mission of the captive division and be a thoughtful regulator.  I know she has the experience and skills and new ideas to help guide the industry forward,” said David Provost, retiring Deputy Commissioner of Captive Insurance.

In 2018, Bigglestone was the recipient of the Business Insurance Women to Watch Award for her leadership, expertise, and accomplishments in the captive insurance industry. Since 2016, she has been named to the Captive Review “Power 50” list, a list made up of the most influential captive professionals in the world, and consistently the top-ranking regulator.

“The Vermont Captive Insurance Association (VCIA) is delighted by the appointment of Sandy Bigglestone, who has a long history within DFR and the captive industry and is recognized as a dynamic and skilled leader and mentor, an outstanding communicator, and a thought leader,” said Kevin Mead, President of the VCIA. “Sandy will ensure stability, consistency, and quality that is the hallmark of regulation in Vermont, while also challenging staff and other stakeholders to develop and improve. “

Since 2018, Bigglestone has served as Chair of the National Association of Insurance Commissioners’ Risk Retention Group Task Force, a working group that is focused on various state, federal, and industry activities impacting risk retention groups.  EIIA staff have created two captive insurance companies in Vermont. The first being College Insurance Company in 2002 and the second, College Risk Retention Group, in 2009.

“We are so grateful to Sandy for her continual willingness to spend the necessary time to understand the operations of our business and guide us accordingly over the years,” said Mary Ellen Moriarty, VP of Property & Casualty at EIIA. “Sandy is a polished professional, goes the extra mile when necessary, and wants to see us thrive. She is the perfect person to guide Vermont.”

Kate Boucher, Vice President, Regulatory & Compliance, Premier Insurance Management Inc. is a captive manager in Vermont who has worked with Sandy throughout her time at DFR. “There have only been a handful of people to hold the title of Deputy Commissioner of Captive Insurance in Vermont and Sandy is truly deserving of the title.  She has served the captive insurance community and the Department with intelligence, dedication, grace and good business sense.”

Bigglestone also serves as the current Chair of the Captive Insurance Companies Association’s Amplify Women™ Education Sub-Committee, working to raise awareness about the captive industry in colleges and universities across the country and is an Advisory Board member to the Business Insurance World Captive Forum.

“Sandy’s dedication to the captive industry, her passion for ensuring that Vermont remains the ‘Gold Standard’ in captive domiciles, her commitment to professional development for women in the industry, and her natural leadership style make her the best choice,” said Tracy Hassett, President, EdHealth. “As a captive owner with a Vermont domiciled captive, I can’t imagine a more superb decision.”

“Sandy Bigglestone has been an essential and long-standing part of Vermont’s captive insurance initiative.  She is a key reason that Vermont has had so much success as a captive insurance domicile.  Her tenure at the Department has been marked by sound judgement and fairness,” said Jeff Johnson, Shareholder and captive attorney, Primmer Piper Eggleston & Cramer PC.

“The Vermont Captive industry and the broader captive sector will be served very well by Sandy Bigglestone,” said John Prescott, Managing Partner, Johnson Lambert LLP. “I’ve known Sandy to be a thoughtful, inquisitive professional and a terrific person. Under her leadership, I’m confident Vermont will continue to be a forward thinking, fair and value-added captive insurance regulator.  She will represent Vermont very well and we look forward to working with her in this new role.”

“Sandy is a natural leader, and we are happy to have her stepping into this role,” said Interim DFR Commissioner Kevin Gaffney. “We look forward to what’s ahead for Vermont’s captive industry.”

“I am thankful for all of the great work in Vermont over the last 40 years, and proud that I have been exposed to 25 years of top-notch leadership and participated in keeping Vermont at the forefront of captive domiciles worldwide,” said Sandy Bigglestone. “Looking ahead, I am elated to continue our tradition of excellence, to model good captive regulation, and to advance Vermont’s footprint.”

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

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