Jeff focuses his practice on the formation, regulation and governance of captive insurance companies. He assists with all matters in the lifecycle of a captive.

Jeff’s clients rely on him for practical business advice to help them reach their goals.  He is known for his creativity, problem-solving and thought leadership.  His long tenure in the industry includes time spent as a captive manager, which gives him a unique perspective.

Jeff has a thorough understanding of the myriad issues that impact captive insurance arrangements.  He is active in a number of industry associations and is a faculty member with the International Center for Captive Insurance Education.

Jeff is a founder and former director of the Delaware Captive Insurance Association and is an active member of several other captive insurance industry associations, working closely with regulators.  He is a director of the Self-Insurance Institute of America and chairs its Enterprise Risk Captive Advocacy Working Group, which focuses on government advocacy for the captive insurance industry.

Jeff also has experience as an entrepreneur, as outside general counsel for small businesses and in business-side positions in financial institutions.

Representative Experience

Any result the lawyer or law firm may have achieved on behalf of clients in other matters does not necessarily indicate similar results can be obtained for other clients.

  • Outside general counsel for a captive manager with operations in 4 domiciles and with 700 captives under management.
  • Assisted a captive manager in resolving regulatory issues and re-domesticating its entire portfolio of clients.
  • Designed and implemented several risk distribution pooling vehicles.
  • Structured and implemented group cell captive arrangement for non-emergency medical transportation brokers.
  • Represented medical stop-loss insurance broker in development and deployment of multiple group captive series LLC.
  • Assisted regional non-profit in transitioning from group captive to pure captive. 
  • Negotiated reinsurance agreement for fronted group captive for the trucking industry.

Professional & Civic Engagement

  • Delaware Captive Insurance Association, Former Director, Founder, Past Chair of Legislative Committee
  • Self-Insurance Institute of America, Inc., Director, Chair of Enterprise Risk Captive Working Group, Past Chair of Captive Insurance Committee
  • Captive Insurance Companies Association, Member
  • North Carolina Captive Insurance Association, Member
  • Tennessee Captive Insurance Association, Member
  • International Center for Captive Insurance Education, Director and Faculty Member
  • Delaware State Bar Association
  • Nevada Bar Association
  • American Bar Association

Thought Leadership

  • AM Best at DCIA interview of Jeffrey K. Simpson