Customer Success Director, Captives

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Customer Success Director, Captives based in United States. This senior client-facing role will lead the operational success of captive insurance relationships from onboarding through renewal. You will serve as the central point of contact for captive owners, brokers, advisors, and internal stakeholders across finance and operations. Your responsibilities will span reinsurance agreements, collateral, cash movements, cessions, onboarding, reporting, and day-to-day client servicing. Working closely with Legal, Treasury, Operations, Actuarial, and Finance, you will remove obstacles and ensure every transaction moves forward on schedule. You will also help establish scalable processes that allow a growing captive portfolio to operate efficiently without unnecessary manual work. The role combines relationship management, operational execution, financial discipline, and cross-functional leadership in a fast-growing, technology-driven insurance environment. It offers significant autonomy, visibility, and the opportunity to shape the operating model of a developing Captive practice.

Serve as the primary day-to-day contact for active captive relationships, acting as the client liaison for operational, contractual, collateral, and financial matters. Own the operational success of captive accounts and ensure issues are identified, escalated, and resolved promptly. Partner with Legal to drive reinsurance agreements and program schedules through completion, tracking open comments, coordinating turnaround, and escalating stalled items. Manage the end-to-end process for establishing trust accounts and letters of credit, including collecting required counterparty information and documentation and coordinating with Treasury until collateral is fully established. Monitor cash receipts, follow up on overdue ceded premiums, and drive timely collection of losses and settlement of quarterly cessions. Lead new captive onboarding from due diligence and internal approvals through accurate setup in back-end systems. Partner with Operations to resolve bordereaux questions and ensure accurate and timely operational processing. Serve as the primary contact for outsourced captive managers, ensuring regulatory requirements are addressed across relevant domiciles and monitoring the establishment of new captive cells. Monitor portfolio performance and unit economics, producing reporting that highlights deal performance and identifying relationships or transactions that may be trending off track. Collaborate across Legal, Treasury, Operations, Actuarial, and Finance to resolve complex issues and maintain momentum across the captive portfolio. Identify opportunities to standardize, automate, and improve operational processes so the practice can scale efficiently as the portfolio grows. Requirements: 7+ years of experience in insurance or reinsurance, ideally in account management, client service, program operations, or a comparable role. Experience with captives, fronting arrangements, delegated authority relationships, or specialty insurance programs. Bachelor’s degree in Business, Finance, Risk Management, or a related field. Professional insurance or risk qualifications such as CPCU, ARe, ACI, or similar are a plus. Strong understanding of reinsurance structures and their accounting implications. Hands-on knowledge of collateral mechanisms, including Regulation 114 trusts, letters of credit, and Schedule F considerations. Experience working with captive domicile requirements and cell formations, including collaboration with outsourced captive managers. Strong client relationship skills, with the ability to communicate credibly and effectively with captive owners, brokers, advisors, and internal stakeholders. Exceptional follow-through and attention to detail, with the ability to identify outstanding agreements, unfunded trusts, delayed cash movements, or other operational gaps and drive them to resolution. Demonstrated ability to lead cross-functional initiatives involving Legal, Treasury, Operations, Finance, and other business functions. Experience influencing senior stakeholders and coordinating multiple parties toward shared deadlines. A continuous-improvement mindset, with a track record of identifying and implementing process, automation, or performance improvements. Ability to build scalable operational processes rather than relying on manual, deal-by-deal solutions. Comfort working with autonomy and managing multiple priorities in a fast-growing, technology-led environment. Benefits: Opportunity to play a pivotal role in building and scaling a captive insurance practice. High-visibility position with significant autonomy and influence across multiple business functions. Direct exposure to captive owners, brokers, advisors, and specialty insurance stakeholders. Opportunity to work across Legal, Treasury, Operations, Actuarial, and Finance. Ability to shape scalable processes, workflows, and operating practices within a growing business. Opportunity to contribute to a technology-driven approach to specialty insurance and risk management. Collaborative environment with broad cross-functional exposure. Opportunity to make a direct impact on client relationships, portfolio performance, and operational execution.

laptop-ats-crawler v3