Director, Risk Management, Workers Compensation & Benefits

Location Type: Remote (USA) Employment Type: Full-Time Salary: $148.4K - $240.9K

About Us

Wrapbook is a smart, intuitive platform designed to streamline production payroll and accounting, making it easier, faster, and more secure. Our unified payroll platform connects production, accounting, cast, and crew in one central location. Wrapbook empowers production teams to manage projects, pay personnel, track expenses, and gain data-driven insights, while enabling workers to manage timecards, track pay, and onboard efficiently from any device. We bring clarity and dependability to production payroll, enhancing team productivity.

Wrapbook is trusted by companies of all sizes and is utilized by top production companies such as SMUGGLER, Tuff, and GhostRobot. Our team comprises over 250 professionals across the USA and Canada, with expertise from entertainment and technology sectors including SAG-AFTRA, DGA, IATSE, Teamsters, Amazon, Microsoft, and Facebook. We are backed by prominent investors like Jeffrey Katzenberg’s WndrCo, Andreessen Horowitz, and A* Capital, and have raised $130M, positioning us for continued growth.

The Opportunity

We are seeking a strategic, cross-functional leader to own and scale two critical areas of Wrapbook’s business: our Workers Compensation program and our in-house Health Benefits offering. As the Director, Risk Management Workers Compensation and Benefits, you will define the vision, build and evolve the operational model, and lead the teams responsible for delivering exceptional service in these domains.

Workers' Compensation

On the Workers' Compensation side, you will oversee end-to-end operations, including underwriting, claims management, compliance, and tooling. You will lead the annual WC renewal process, collaborate with Finance on large-loss forecasting, and shape the long-term Workers' Comp strategy, particularly as we expand further into Film & TV. You will also drive the evolution of our tooling and customer UI in partnership with our Product and Engineering teams.

Health Benefits

For our Benefits side, you will serve as the business lead for Wrapbook’s in-house health benefits offering. You will be responsible for the strategy, execution, and ongoing optimization of the program, working closely with cross-functional partners. This includes owning the complete employee journey, from enrollment and onboarding through deductions and offboarding. You will be accountable for scaling service delivery, cultivating strong relationships with third-party vendors, and providing regular updates and strategic recommendations to the Executive team regarding the future of our benefits strategy.

This is a strategic and hands-on leadership role that demands deep domain expertise, excellent cross-functional collaboration skills, and a strong bias toward execution. You will be instrumental in shaping Wrapbook’s Risk and Benefits operations for future scale.

What You'll Do

Workers’ Compensation Procurement, Renewal & Claims Management Leadership

• Own and execute Wrapbook’s WC program strategy across underwriting, claims, compliance, and reporting.
• Act as the primary liaison with TPAs, carriers, brokers, and managed care providers to ensure efficient and compassionate claims resolution.
• Design and implement a customer-first claims experience, prioritizing both speed and empathy for injured workers.
• Drive tooling enhancements in partnership with Product and Engineering to improve automation and user experience for both internal teams and clients.
• Oversee the annual WC renewal process and collaborate with Finance on loss forecasting and reserve strategies.
• Lead the procurement and renewal of workers’ compensation insurance policies, managing relationships with brokers and carriers to ensure optimal coverage, pricing, and compliance across all operating jurisdictions.
• Partner with Finance to forecast program exposure, recommend a loss pick, and manage the program’s performance over time.
• Analyze historical data to identify trends and opportunities for program improvement and cost reduction.