Vermont Appoints Dylan Moss as Assistant Chief Examiner
The appointment updates leadership for the state department overseeing the financial solvency of captive insurance entities.
Updated on Oct. 21, 2026 in Insurance
The Vermont Department of Financial Regulation has appointed Dylan Moss as its new assistant chief examiner. Moss, who joined the agency in 2024, moves into this leadership role after previously serving as an insurance examiner-in-charge.
Why it matters
This appointment signals a shift in leadership at the state agency that provides regulatory oversight for captive and risk retention group insurance companies operating in Vermont. Stability in these supervisory roles can impact how insurance solvency standards are applied to these specialized risk entities.
Moss brings over six years of prior private-sector experience from USAA to his new post. His oversight responsibility covers the financial solvency analysis of captive and risk retention group insurance companies within the state.
The players
Dylan Moss
The newly appointed assistant chief examiner for the Vermont Department of Financial Regulation with a background in private-sector insurance claims.
Vermont Department of Financial Regulation
The state agency responsible for overseeing insurance companies, including captive and risk retention groups, to protect policyholder financial interests.
The details
As assistant chief examiner, Moss will oversee the department's staff responsible for auditing and analyzing the financial health of captive insurers and risk retention groups. This role involves maintaining the state's regulatory framework through risk-focused solvency analysis to ensure that these specific insurance entities remain capitalized to meet their obligations. Moss previously managed these examinations in his capacity as insurance examiner-in-charge.
Timeline
January 2024: Moss joined the DFR as insurance examiner II.
July 2024: Moss promoted to insurance examiner III.
April 2025: Moss began serving as insurance examiner-in-charge.
October 2026: Moss promoted to assistant chief examiner.
Money Landscape
Vermont maintains a globally recognized regulatory environment for captive insurers and risk retention groups. This personnel change reflects the department's internal career progression cycle within that established oversight framework.
While this appointment is administrative, it influences how the state supervises the solvency of captive and risk retention group insurers. Residents involved in these insurance arrangements should consult with a professional to understand if regulatory shifts affect their specific coverage security.
The takeaway
The appointment of a new assistant chief examiner marks a transition in the oversight leadership for captive insurance companies in Vermont. Residents and businesses holding such policies should track future department communications regarding solvency standards.
Further reading
Learn more about the state's oversight of insurance products in our Insurance section.
Source note: This article includes information reported by Captiveinsurancetimes.
