The Opportunity - Senior Manager, Risk Operations (Remote - USA / Canada) Wrapbook is the entertainment industry's leading payroll and employer-of-record (EOR) platform. Our Risk & Benefits Operations division manages four critical service lines-Workers' Compensation, Benefit Operations, Unemployment Insurance, and Company Insurance-protecting tens of thousands of project workers across hundreds of productions annually.
We are looking for a Senior Manager, Risk Operations to lead the full scope of our Workers' Compensation program-spanning claims oversight, risk mitigation, underwriting operations, and day-to-day program administration-while bringing a risk management mindset to how we run and improve it. This is a player-coach role: you will manage a team of specialists while personally owning operational outcomes across the entire WC program lifecycle.
This role reports directly to the Senior Director, Risk & Benefits Operations.
What You'll Do: Claims oversight and loss performance- Serve as the primary operational point of contact for our TPA (Sedgwick), managing claim handling expectations, reserving practices, and escalation protocols
- Monitor and analyze loss runs, claim frequency/severity trends, and open claim inventory; surface insights to the Sr. Director and drive corrective action with the team
- Review large loss and litigated claims on a regular cadence, ensuring the TPA's handling strategy aligns with program objectives
- Track SLA compliance and claims quality metrics, holding the TPA accountable to performance standards
- Identify patterns in claims data (by state, classification, production type, time of year) and translate findings into actionable recommendations for risk reduction
Risk management and WC program administration- Develop and implement risk mitigation initiatives such as safety programs, return-to-work protocols, and claims management best practices tailored to entertainment industry workflows
- Use claims and underwriting data together to identify where operational improvements (better classification, faster reporting, targeted safety guidance) can reduce loss frequency and severity
- Drive the end-to-end underwriting operations workflow-production company onboarding, classification, state jurisdiction setup, and policy endorsement execution
- Tracking and reporting on Worker Compensation KPIs and SLAs across the WC program
Team leadership- Manage, mentor, and develop Workers Compensation Operations and Claims Specialists
- Set clear goals, run regular 1:1s, and drive accountability across all program areas-claims, risk mitigation, underwriting operations, and COI workflows
- Balance team workload across the claims and underwriting functions, adjusting capacity allocation as production seasons and claim volumes shift
- Partner with the Sr. Director on capacity planning, hiring, and team development as the program scales
AI, knowledge & competitive intelligence- Leverage AI tools (including Claude, Dust, and emerging platforms) as a core part of daily operations-driving research, drafting, workflow automation, and overall team AI capability development
- Build and maintain a centralized Workers' Compensation knowledge base; partner with AI Champions to design and deploy self-serve agents that reduce friction for internal teams and accelerate decision-making
- Serve as Wrapbook's internal subject matter expert on WC program structures-continuously monitoring the landscape, identifying differentiation gaps, and delivering strategic insights to senior leadership
What You'll Have: Required- 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
- 4+ years of people management experience, ideally in a fast-growing or high-volume environment
- 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
- 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 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
- Excellent communication skills with the ability to translate WC concepts for non-insurance stakeholders
Preferred (strong pluses)- 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
- Experience in entertainment, media, or staffing industry WC programs
- Familiarity with employer-of-record (EOR) or professional employer organization (PEO) risk structures
- ARM, CPCU, or equivalent risk management designation (or in progress)
- Experience with Sedgwick or comparable national TPA platforms
Why Join UsAt Wrapbook, creativity meets technology - and not just in the product.
In addition to a competitive salary and all the benefits you can expect from a fast-growing technology company, you'll get access to a team of creative problem solvers and the chance to see your contributions make large impacts. Benefits include:
- Unlimited Paid Time Off
- Work from anywhere in Canada and USA
- Health and Dental benefits
- Up to $1,500 USD/ $2,025 CAD towards IT set up for your home
- Up to 2% matching RRSP / 401K
- Learning and Development opportunities
- Up to $50 USD/ $67.50 CAD towards Internet/Cell phone service
Apply NowHave we got your attention? Submit your application today and a member of our Talent team will be in touch with you shortly!
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