Wrapbook

Director, Risk Management, Workers Compensation & Benefits

Remote

$148,400 – $240,900Compensation
Expert & Leadership (9+ years)Experience Level
Full TimeJob Type
UnknownVisa
Biotechnology, Financial Services, Insurance, EntertainmentIndustries

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.

Skills

Workers Compensation
Health Benefits
Underwriting
Claims Management
Compliance
Risk Management
Strategic Planning
Operational Model Development
Financial Forecasting
Insurance

Wrapbook

Digital payroll and production management platform

About Wrapbook

Wrapbook offers a digital payroll and production management platform tailored for the entertainment industry, serving clients like film and TV production companies. The platform simplifies payroll by allowing users to collect timecards through an app, generating smart timecards that ensure compliance with industry standards. It stands out from competitors by integrating with accounting software like QuickBooks, streamlining financial management. The goal of Wrapbook is to provide a fast and secure way to manage payroll and production needs, reducing administrative burdens for its clients.

Toronto, CanadaHeadquarters
2018Year Founded
$146.3MTotal Funding
LATE_VCCompany Stage
Enterprise Software, Financial Services, EntertainmentIndustries
201-500Employees

Benefits

Unlimited Paid Time Off
Remote Work Options
Health Insurance
Dental Insurance
Home Office Stipend
401(k) Company Match
401(k) Retirement Plan
Professional Development Budget
Phone/Internet Stipend

Risks

Increased competition from established players like Cast & Crew threatens market share.
Entertainment industry strikes may disrupt production schedules, affecting Wrapbook's service demand.
Reliance on third-party integrations poses risks if partners change APIs or business models.

Differentiation

Wrapbook offers a unified platform for production payroll and cost management.
The platform ensures compliance with industry standards through smart timecards and union compliance.
Wrapbook integrates with major accounting software, enhancing financial management efficiency.

Upsides

Wrapbook's recent $20M funding will accelerate its NextGen payroll solution development.
The platform's new cost-management tools improve collaboration between production and accounting teams.
Growing demand for digital payroll solutions in entertainment boosts Wrapbook's market potential.

Land your dream remote job 3x faster with AI