The Captive Insurance Division of the Vermont Department of Financial Regulation focuses on maintaining a regulatory system that attracts quality business to Vermont, promotes the state reputation in the industry, and safeguards the solvency of captive insurers while recognizing the special purpose for which they were created. The division pursues its mission by:
- Attracting and licensing quality programs whose primary purpose is risk management or risk financing;
- Performing ongoing financial surveillance;
- Performing periodic financial examinations;
- Implementing and enforcing laws and regulations;
- Developing effective and reasonable policies and procedures; and
- Advancing the growth of Vermont’s captive industry.
Deputy Commissioner Sandy Bigglestone
As Deputy Commissioner of the Department of Financial 
Regulation Captive Insurance Division, Sandy Bigglestone oversees an extensive team of examiners, analysts and administrative staff responsible for the administration and regulation of captive insurance companies and risk retention groups.
Deputy Commissioner Bigglestone transitioned into her current leadership position in September 2022, capping over a quarter century career in the captive insurance industry. A highly regarded regulator among industry peers, Ms. Bigglestone has been part of the DFR Captive Insurance Division since 1997, serving the last 14 years as principal staff member to her predecessor. She holds an Associate Professional in Insurance Regulation designation from the National Association of Insurance Commissioners and is a Certified Public Accountant, Certified Financial Examiner, and Certified Public Manager with the State of Vermont. In 2018, Business Insurance awarded her the Women to Watch Award for her leadership, expertise and accomplishments in the captive insurance industry, and the 2024 Captive Review Power 50, which recognizes professionals having the most influence within the global captive insurance industry, lists her at #1.