We are seeking an experienced and strategic Director of Finance to lead financial operations for a portfolio of captive insurance companies. This role is responsible for overseeing financial reporting, regulatory compliance, client service delivery, and team leadership within a captive management environment.

The ideal candidate brings deep expertise in reinsurance and insurance accounting (GAAP/STAT/IFRS), strong client-facing skills, and experience managing multiple captive programs across diverse lines of business.

Key Responsibilities

Financial Oversight & Reporting

Oversee monthly, quarterly, and annual financial reporting for a portfolio of captive insurance clients
Ensure accuracy and timeliness of financial statements in accordance with GAAP, STAT, IFRS and regulatory requirements
Oversee the preparation of audited financial statements and coordinate with external auditors
Develop, manage and monitor the annual Budget and Forecast for the captive management company, along with regularly analyzing variances between budget and actual to support informed decision making

Regulatory & Compliance

Coordinate with Compliance to ensure adherence to domicile-specific regulations
Oversee preparation and filing of statutory financial statements and regulatory reports
Maintain strong relationships with regulators and ensure adherence to captive insurance laws

Client Relationship Management

Serve as the primary financial contact for clients, boards, and shareholders
Present financial results and insights at board meetings
Provide strategic financial guidance, including capital adequacy, dividend planning, and risk analysis

Leadership & Team Management

Lead, mentor, and develop a team of finance and accounting professionals
Manage workload allocation across multiple client engagements
Foster a high-performance, client-focused culture

Strategic & Operational Support

Support captive formations, feasibility studies, and financial modeling
Partner with underwriting, actuarial, and operations teams
Drive process improvements and implement best practices across the finance function

Qualifications

Bachelor’s degree in Accounting, Finance, or related field (CPA strongly preferred)
8–12+ years of experience in insurance or captive management accounting
Strong knowledge of GAAP, Statutory and IFRS accounting principles
Experience with captive insurance structures (Single-parent, reinsurance, group captives, RRGs, etc.)
Experience with lines such as GL, PL, Property, Workers Compensation and other non-traditional risks
Proven leadership experience managing teams and client relationships
Excellent communication and presentation skills

Preferred Experience

Reinsurance Accounting experience
Experience working with multiple domiciles (U.S. and offshore)
Background in public accounting or consulting within insurance/captives
Experience with financial systems and reporting tools

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MSI, part of The Baldwin Group

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