Senior Manager of Risk Operations

Join Wrapbook, the leading payroll and employer-of-record platform in the entertainment industry. As the Senior Manager of Risk Operations, you will lead our Workers' Compensation program, overseeing claims, risk mitigation, underwriting operations, and day-to-day administration. This player-coach role involves managing a team of specialists while personally owning operational outcomes across the entire WC program lifecycle. You will report directly to the Senior Director of Risk & Benefits Operations and be responsible for driving risk reduction initiatives, managing vendor relationships, and leveraging AI tools to enhance operations.

• Lead the full scope of the Workers’ Compensation program, including claims oversight, risk mitigation, underwriting operations, and day-to-day program administration.
• Manage a team of specialists while personally owning operational outcomes across the entire Workers’ Compensation program lifecycle.
• Serve as the primary operational point of contact for the Third-Party Administrator (TPA), managing claim handling expectations, reserving practices, and escalation protocols.
• Experience using claims and policy data to identify trends, build reports, and recommend operational improvements
• Demonstrated ability to manage vendor and broker relationships with a bias toward accountability and measurable outcomes
• 4+ years of people management experience, ideally in a fast-growing or high-volume environment
• Excellent communication skills with the ability to translate WC concepts for non-insurance stakeholders
• Solid knowledge of WC claim lifecycles, reserving practices, and TPA performance management
• Strong understanding of WC policy structures, classification systems, payroll-based premium calculations, and audit processes
• 5–8+ years of experience in workers’ compensation operations, insurance program management, or a related risk management function—with exposure across claims and underwriting/policy administration
• A risk management orientation—you naturally connect underwriting decisions to claims outcomes and look for ways to reduce loss frequency and severity across the program
• Experience with large-deductible or self-insured WC program structures (vs. guaranteed-cost only)
• Familiarity with actuarial reports, loss development data, and how they inform program decisions
• Familiarity with employer-of-record (EOR) or professional employer organization (PEO) risk structures
• ARM, CPCU, or equivalent risk management designation (or in progress)
• Experience in entertainment, media, or staffing industry WC programs
• Experience with Sedgwick or comparable national TPA platforms