Director of Finance

Job Overview

Director of Finance & Accounting

Complete Captive Management Services, LLC (DBA Complete Captive)

About Complete Captive

Complete Captive Management Services, LLC (“CCMS”) is a captive insurance manager overseeing medical stop-loss captives. CCMS is responsible for the financial integrity, regulatory reporting, and operational infrastructure that support these captives and their participating cell owners.

Position Overview

The Director of Finance is responsible for the end-to-end cash flow process and the preparation and presentation of unaudited financial statements for CCMS and its managed captives. Financial statements are the cornerstone of sound insurance company operations and of CCMS' reporting obligations to regulators, actuaries, and insureds.

The Director will be fluent in the mechanics unique to a captive and reinsurance structure: cash deposits, premium and claim loss allocations, claims payments, ceding and retrocession flows across participating captives, and profit distributions at period close. Cash movements between related entities are booked similar to intercompany assets and liabilities — this cycle repeats monthly and must reconcile cleanly across every cell and pool participant.

A core priority for this role is ensuring CCMS' captive accounting practices, reporting cadence, and financial statement presentation remain consistent with the standards and conventions used by admitted stop-loss carriers. The Director will be expected to benchmark CCMS's internal financial processes against admitted-market norms and recommend adjustments where our captive structures should mirror, or clearly justify departing from, those conventions.

As a growing organization, financial processes and policies are continually evolving alongside client needs and regulatory change. The Director is expected to author, maintain, and version CCMS' finance-related policies and procedures using the company's standard numbered policy format, and to work closely with the Chief Operating Officer and Staff Accountant(s) on daily operations.

The Director will also represent CCMS in front of third parties — including retrocession/reinsurance actuaries, state regulators, finance committees, and client cell owners — on financial and reporting matters.

Key Responsibilities

• Own the full cash flow lifecycle across CCMS' managed captives: deposits, intercompany transfers and allocations, pool charge and excess/quota-share reconciliation, claims payments, and profit distributions at period close
• Prepare and present unaudited financial statements for CCMS and its captive clients, including retrocession/pooling reconciliations against gross written premium
• Benchmark CCMS accounting and reporting practices against admitted stop-loss carrier conventions and recommend alignment where appropriate
• Collaborate daily with the Staff Accountant(s) and report directly to the Chief Operating Officer
• Author, review, and maintain CCMS' finance policies and procedures under the company's numbered policy system, including required review cycles
• Advise CCMS executives on financial findings, cash position, and reporting risk
• Lead scheduling, agenda-setting, and presentation for finance committee meetings
• Serve as the primary financial point of contact for engaged third-party actuaries and regulatory auditors
• Support due diligence and financial reviews tied to new captive cell onboarding and treaty year transitions

Required Skills & Experience

• Proven experience as a financial controller or in a comparable senior accounting role
• Direct experience with insurance, reinsurance, or captive accounting — intercompany cash flow, premium/claims reconciliation, and period-close processes
• Strong problem-solving and critical-thinking skills, with sound judgment on when to escalate versus resolve independently
• Comfortable operating in a small, fast-moving team environment with direct executive visibility
• Willingness and ability to adopt new technology to improve workplace efficiency
• Proficiency with MS Office, secure email/document workflows, and CRM platforms such as Salesforce

Preferred Skills

• Experience specifically within the stop-loss, reinsurance, or captive insurance sector
• Familiarity with admitted stop-loss carrier reporting conventions or prior experience at a carrier, MGU, or TPA
• Exposure to actuarial reporting cycles, retrocession treaty structures, or protected cell captive facilities

Education Requirements

• Bachelor's degree in Accounting or Finance
• Certified Public Accountant (CPA) license in good standing

Position Details

• Full-time (40 hours/week), Monday–Friday, 8:30 am–5:00 pm
• On-site preferred; remote can be accommodated
• On-site training required at CCMS's office in the Northern suburbs of Pittsburgh, PA
• Benefits: paid time off, bonus opportunity, cell phone stipend
• Compensation: based on experience

Pay: $130,000.00 - $175,000.00 per year

Benefits

• 401(k) matching
• Dental insurance
• Health insurance
• Health savings account
• Paid time off
• Vision insurance

Work Location: Hybrid remote in Pittsburgh, PA 15237