Captive Consultant; Business Development

Key State is seeking a Captive Consultant to drive the profitable growth of our Captive Practice by leading feasibility studies, expanding mature captives, building and strengthening broker and fronting and reinsurance partnerships, generating qualified opportunities through targeted industry engagement, and providing underwriting support to existing captives to ensure long-term performance and sustainability. The ideal candidate brings strong underwriting judgment, financial and actuarial literacy, and boardroom presence with the ability to translate complex structures into executive-ready recommendations and long-term captive strategies.

• Lead data-driven feasibility analyses (5-10 years of loss data, total cost of risk) to recommend optimal retentions, layering, and capital strategies.
• Evaluate fronting options and reinsurance markets; prepare underwriting-ready submissions.
• Identify additional lines suitable for phased captive expansion and position Key State as a long-term strategic advisor.

• Provide disciplined underwriting guidance across assigned captives, including risk selection standards, pricing adequacy, and trend assumptions.
• Analyze loss development and reserves; recommend corrective actions (pricing, limits, retention).
• Support renewal negotiations with data-backed narratives for fronting carriers and reinsurers; assist with policy wording, coverage structure, and limits.

• Design layered programs and reinsurance towers; optimize capital efficiency and collateral.
• Coordinate with actuaries and brokers on pricing and reserving assumptions; develop market submission materials.
• Segment risk to reduce volatility, and improve long-term captive performance.
• Maintain active relationships with multiple fronting partners and reinsurers as well as brokers.
• Evaluate collateral and cost-of-capital impacts; assist in negotiating terms and securing capacity.

• Represent Key State with technical authority at targeted industry events (e.g., CICA, VCIA); conduct pre-event outreach and structured post-event follow-up.
• Participate in panels or round tables when appropriate and generate qualified feasibility discussions that translate into captive formations.

• Conduct annual strategic and underwriting reviews; recommend new lines (e.g., cyber, GL, professional liability) and structural optimizations.
• Drive expansion within mature captives while sustaining high client retention.

• 5-10 years of underwriting or alternative risk/captive experience.
• Strong financial and actuarial literacy; ability to interpret loss triangles, pricing models, reserves, and capital requirements.
• Experience underwriting commercial lines programs and structuring layered reinsurance/fronting arrangements.
• Executive-level communication and presentation skills (board and C-suite).
• Entrepreneurial mindset aligned with a growth platform; high ownership and follow-through.

• Prior work with fronting carriers and reinsurers; proven ability to produce underwriting-ready submissions.
• Familiarity with feasibility processes, types of captive structures, and captive expansions across multiple lines.
• Professional designations (e.g., ACI, CPCU, ARM, CPA) are a plus.

Key State offers a competitive compensation structure designed to reward performance, long-term relationship development, and growth. Compensation includes:

• Performance-based incentive opportunities.
• Comprehensive benefits including health, dental, vision, and retirement plan.

Total compensation is commensurate with experience, education and qualifications.

This role may be based in Key State's Vermont office or remote (U.S.), with periodic travel to client sites, carriers, reinsurers, and industry conferences. At Key State, we value all employees and job candidates as unique individuals and welcome the variety of experiences they bring to our company. We maintain a strict non-discrimination policy and believe everyone should be treated equally regardless of race, sex, gender identification, sexual orientation, national origin, native language, religion, age, disability, marital status, citizenship, genetic information, pregnancy, or any other characteristic protected by law.

Founded in 1991, Key State is a rapidly growing, privately held financial services firm specializing in providing tax-advantaged investments to community banks. With over $18 billion in assets under management, Key State has managed investment subsidiaries for community banks for over 35 years.

Since launching its captive management practice in 2008, Key State has formed and managed captives for over 100 companies across the U.S.

In 2019, Key State launched a renewable energy tax credit investment platform for community banks. Key State helps community…