Jesse Crary

ICCIE Elective Course: Captive Board Governance

Jesse Crary concentrates his practice on captive insurance, commercial transactions, regulatory compliance and general corporate matters. Through his extensive work representing and advising captive insurance companies and risk retention groups, he has developed strong relationships with insurance regulators and leading captive service providers. Jesse is a specialist and leading attorney in the area of group medical stop loss captives.

Jesse helps clients develop integrated benefit programs that combine the administration of employee benefit plans with access to captive medical stop loss coverage, and provides valuable assistance navigating the complexities of insurance and benefits-related laws and regulations. Jesse has extensive experience forming and providing ongoing corporate and regulatory counsel to single parent, group, sponsored and protected cell captive insurance entities, as well as risk retention groups.

Practice Areas:

Captive Insurance
Financial Services & Banking

Admitted to Practice:

Vermont Bar
U.S District Court for the District of Vermont
District of Columbia Bar

Professional Affiliations:

Vermont Bar Association
Vermont Captive Insurance Association Finance Committee


Vermont Law School, J.D. 2006
University of Vermont, B.A. 1996

Pro Bono & Volunteer Work:

United Way Workplace Ambassador
Head Coach, Richmond VT Little League

Speaking Engagements:

Presenter, “Efficient Legal Structures for Group Medical Stop Loss Captives”; Captive Insurance Conference of America 2015
Presenter, “Cell Captives: Uses and Best Practices”; Vermont Captive Insurance Association Conference 2015


Captive Board Governance