Assistant Controller

Description

Partner with the CFO on financial strategy, capital planning, and the implementation of new captive structures.

Support external audit and actuarial review processes by compiling schedules, source data, and reconciliations.

Lead the month-end and year-end close process for entities, including journal entries, reconciliations, and accruals.

Maintain strong internal controls, accounting policies, and documentation to ensure regulatory readiness and audit compliance.

Prepare and submit quarterly and annual regulatory filings, including NAIC schedules, RBC calculations, and domicile-specific requirements.

Support preparation of financial reporting for employer groups within captive cells, including premium allocations, claims activity, and financial summaries as required by structure and governance.

Ensure timely and accurate premium, claims, and reinsurance reconciliations with TPAs, carriers, and fronting partners.

Manage and reconcile revenue tracking across Gross Written Premium (GWP), Gross Revenue, and Net Revenue for both KPI reporting and GL entries; ensure alignment with system-of-records and revenue recognition tools (e.g., RightRev).

Manage investment account activity, cash flows, and trust account reporting for each captive structure.

Oversee accounting for premiums, claims, reserves, reinsurance activity, and intercompany pooling or eliminations.

Collaborate with actuarial, underwriting, and operations teams to ensure accounting accuracy and business alignment.

Manage preparation of GAAP and statutory financial statements, including coordination with auditors and captive managers.

Requirements

Proficiency in accounting systems and Excel; ESL Office experience a plus.

Hands-on experience with financial audits and actuarial reserve processes.

Prior experience preparing or reviewing financials for captives, MGUs, or reinsurers.

3-7 years of accounting experience, with significant exposure within the insurance, reinsurance, or captive space.

Experience working with third-party administrators, fronting carriers, and captive managers.

Must be eligible to work in the United States, unable to provide sponsorship at this time.

Strong knowledge of regulatory filing requirements and financial controls for captives.

Bachelor s or advanced degree in finance, accounting, or related field with CPA preferred.

The Assistant Controller, Insurance & Reinsurance Operations, is responsible for overseeing all accounting, financial reporting, and regulatory compliance for insurance and reinsurance programs. This role requires deep knowledge of insurance accounting principles, experience working with captive managers and fronting carriers, and the ability to manage close processes, financial audits, and regulatory filings across multiple jurisdictions.

Deep understanding of GAAP and statutory accounting principles applicable to insurance entities.

Benefits

Health benefit solutions should be as unique as the businesses they serve. The thing employers have most in common is the problem they are trying to solve, yet that doesn’t mean it is the same solution for everyone. Purpose-driven Alternative Funding Platform for small to mid-sized employers – harnessing the power of a community of businesses to generate market-leading discounts on medical stop-loss insurance, provider networks, cost containment solutions, and member navigation tools. We strive to enhance the quality of care and member experience while decreasing avoidable costs.

This is a Hybrid position; on-site 2-3 days per week.

Training + Development

Interview process

Visa Sponsorship

Security clearance