Head of Finance - Captives

Built on meritocracy, our unique company culture rewards self-starters and those who are committed to doing what is best for our customers.

The Head of Finance – Captives is a strategic financial leader responsible for shaping the vision, governance, and financial direction of the organization’s captive insurance operations. This role drives long-term value by ensuring regulatory compliance, optimizing financial performance, and aligning captive strategies with overall business objectives, while collaborating closely with executive leadership, risk management, and external advisors.

How you will contribute:

• Establish, monitor, and continuously enhance internal control frameworks and financial governance practices to ensure accuracy, safeguard assets, mitigate risk, and support compliance with accounting standards, regulatory requirements, and audit expectations.
• Direct the preparation, review, and submission of GAAP and statutory financial statements for captive insurance entities, ensuring the completeness, accuracy, and timely reporting of all premium, claims, reinsurance, reserve, and investment activities in accordance with applicable accounting principles and regulatory requirements
• Manage relationships with auditors, actuaries, and tax advisors to ensure timely completion of audit requirements, implementation of recommendations, and overall financial credibility and operational soundness
• Lead financial strategy and performance management by analyzing loss ratios, reserves, investment income, and capital, evaluating captive performance and profitability, supporting pricing, capitalization, and reinsurance decisions, and developing long-term strategies to ensure financial sustainability and alignment with enterprise risk objectives
• Partner with risk management, underwriting, and business leaders on premiums, program design, and funding, assess the financial impact of policy and reinsurance decisions, and provide modeling support to ensure the captive’s finances align with business needs and risk strategy
• Provide strategic oversight of cash flow, liquidity, investments, and capital reserves to safeguard financial stability, optimize funding for potential losses, and ensure full compliance with governance and policy standards
• Manage relationships with service providers of TPAs, actuarial firms, investment managers, and auditors, managing relationships, negotiating contracts, and monitoring performance to ensure cost-effective, high-quality service across all captive functions
• Mentor and develop a high-performing finance team to support captive operations and broader organizational objectives.

Skills & Experience to Be Successful: 

• Bachelor’s degree in Accounting, Finance, or a related field; CPA or equivalent designation preferred.
• 10+ years of progressive finance experience, including leadership roles within insurance, reinsurance, or captive management.  Background within the captives and reinsurance areas are a big plus.
• Strong knowledge of statutory accounting, regulatory frameworks, and captive structures (single-parent, group, or rent-a-captive).
• Demonstrated ability to lead strategic financial initiatives and partner effectively with cross-functional teams.
• Excellent analytical, communication, and executive presentation skills.

Teammate Benefits & Total Well-Being

We go beyond standard benefits, focusing on the total well-being of our teammates, including:

• Health Benefits: Medical/Rx, Dental, Vision, Life Insurance, Disability Insurance  
• Financial Benefits: ESPP; 401k; Student Loan Assistance; Tuition Reimbursement 
• Mental Health & Wellness: Free Mental Health & Enhanced Advocacy Services
• Beyond Benefits: Paid Time Off, Holidays, Preferred Partner Discounts and more. 

Not reflective of all benefits. Enrollment waiting periods or eligibility criteria may apply to certain benefits. Benefit details and offerings may vary for subsidiary entities or in specific geographic locations.

The Power To Be Yourself 

As an Equal Opportunity Employer, we are committed to fostering an inclusive environment comprised of people from all backgrounds, with a variety of experiences and perspectives, guided by our Diversity, Inclusion & Belonging (DIB) motto, “The Power to Be Yourself”.