Former Vermont Captive Regulator Bigglestone Joins SRS as Managing Director

Strategic Risk Solutions (SRS), an independent manager of insurance companies including captives, announced the appointment of Sandy Bigglestone as managing director/chief officer for Governance, Regulatory and Compliance.

Beginning in January 2026, Bigglestone will ensure the firm’s clients have best in class governance procedures in place and are in compliance with regulations that impact captive owners in various jurisdictions.

She will also be involved in the recently announced specialized initiative – SRS Titanium – in serving captive insurance management and consulting for Fortune 500 and other global and complex organizations.

Bigglestone will be based in Vermont, where she most most recently served as the deputy commissioner of the Captive Insurance Division at the Vermont Department of Financial Regulation.(DFR). Over her 29-year career at the state level, she helped establish Vermont as a leader in captive insurance regulation. She has also been actively involved with National Association of Insurance Commissioner (NAIC) and other industry bodies in promoting appropriate regulation of captives and other insurance entities.

The SRS announcement comes just days after the Vermont DFR announced Bigglestone would be leaving the state’s captive division effective Jan. 1, 2026. Bigglestone’s career in state government began in 1997.

Concord, Massachusetts-headquartered SRS has more than 25 years of experience providing management and consulting services to various insurance company entities, from single-parent captives to complex commercial insurers and reinsurers. SRS has operations in the United States, Canada, Europe, Barbados, Bermuda, the Cayman Islands, Latin America, and South Africa.

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