Director of Captives (Insurance)

Comp: $200K to $300K+ (bonus, incentives, etc.)

About the Company:

The company is a diversified insurance firm providing custom, self-funded healthcare solutions to a limited distribution network of brokers, consultants, and agents nationwide. Ranked on the Inc. 5000 Fastest Growing Companies and Best Workplaces, they leverage industry expertise, superior talent, data analytics, and a disruptive mindset to manufacture, underwrite, and administer agile, transparent, and cost-saving solutions.  They optimize the fragmented health benefits supply chain to reduce health benefit costs and create better outcomes for employers and employees.

At the company, people come first. They strive to make a positive impact on the people they serve. They believe this starts with the passion and purpose of their team. Their company culture is rooted in alignment, innovation, and integrity.

About the Job:

The company is seeking to hire a captive insurance professional to design, develop, implement, and represent captive management operations as a new product line within the existing portfolio. This position is expected to

focus on expanding the organization’s strong reputation into the captive management marketplace. Supervisory oversight for the captive client portfolio focusing on ensuring that all services, deliverables, and regulatory compliance items are met. This role will evaluate client opportunities and implement new captive programs. At the direction of clients, this position may serve as a Director, Officer, and/or equivalent position with various captive insurance clients. Attending and participating in industry associations, networking, educational, and promotional events is expected.

Works on the most complex issues with little or no precedent where analysis of situations or data requires an in-depth evaluation of variable factors. Exercises judgment in selecting methods, techniques, and evaluation criteria for obtaining results. This individual is considered a subject matter expert and often recognized as an industry expert by external connections.

Lead architect for captive program initiatives through design, development, implementation, and ongoing program management. Functions as the project manager for the development and implementation of new programs. Determines objectives, directs programs, develops strategies and policies. Develops and implements captive guidelines to comply with claim reporting provisions under insurance/reinsurance policies for internal and third-party claims administrators. Proactively assesses risk to establish new captive programs, systems, and procedures to protect organizational assets.

Conducts ongoing reviews of captive program performance and financial statements issued by captive management accountants and confirms accuracy of annual reporting of captive activity. Spearheads reports with captive actuaries annually to determine funding and retention levels of captive programs.

Duties & Responsibilities:

  • Knowledge of self-funded plans, captive programs, and employee benefits
  • Experience supporting the development of proposals to brokers/clients and maintaining ongoing relationships
  • Defines strategic objectives and policies to ensure and develop risk financing budgeting
  • Develop business plans and financial projections for new captives
  • Provide supervision and oversight of services to complex captive insurance clients
  • Perform special requests, which may include business plan changes, preparing financial proformas, or analyzing new agreements
  • Assist in evaluating if a captive program is right for prospective clients
  • Responsible for developing and implementing individual marketing strategy
  • Manage and increase membership in assigned accounts
  • Responsible for premium growth through existing renewals and new business development
  • Participate in on site visits
  • Participate in board meetings
  • Formulate price estimates and proposals with team members and functional groups using standard models
  • Responsible for directing contractual negotiations and assisting/participating in the negotiations as necessary
  • Track and report on the status of all proposals
  • Communicate back to internal groups the outcome of the negotiations/proposals i.e., clear details, critical time frames, and expectations
  • Develops and completes budget assumptions, in collaboration with actuarial and finance, as needed, for all programs to effectively manage insurance costs.
  • Maintains a high level of knowledge, authority, and independence to serve as an insurance/risk finance subject matter expert and resource for the organization and senior management team.
  • Effectively communicates with internal and external stakeholders including executive leaders. This includes the ability to create and present technical and statistical data and information to all levels of leadership within the organization.
  • Develops and maintains collaborative relationships within the organization to support risk identification, risk solutions and loss prevention initiatives. Manages activities related to staffing, including hiring, orienting, evaluating, disciplinary actions, and continuing education initiatives.
  • Perform other related duties incidental to the work described herein

Essential Qualifications & Skills:

  • Bachelor’s degree in business, accounting, marketing/sales, or other related discipline
  • At least ten (10) years of experience in captive insurance business development, traditional risk financing, and/or alternative risk financing
  • At least five (5) years people and P&L leadership
  • Associate in Captive Insurance, preferred
  • MBA or advanced degree, preferred
  • Experience in preparing financial statements with GAAP, preferred
  • CPA or equivalent (i.e., Chartered Accountant), preferred

Travel: Domestic travel is required for this position


  • Medical insurance
  • Vision insurance
  • Dental insurance
  • 401(k)
  • Disability insurance


Don’t see an opportunity that fits what you are looking for? Reach out to see what else might be in our pipeline.

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