About Us:
Wrapbook is a smart, intuitive platform that makes production payroll and accounting easier, faster, and more secure. We provide a unified payroll platform that seamlessly connects your entire team—production, accounting, cast, and crew—all in one place. Wrapbook empowers production teams to manage projects, pay cast and crew, track expenses, and generate data-driven insights, while enabling workers to manage timecards, track pay, and onboard to new projects from any device. Wrapbook brings clarity and dependability to production payroll, while increasing the productivity of your whole team.
Trusted by companies of all sizes, Wrapbook powers payroll for some of the industry’s top production companies, including SMUGGLER, Tuff, and GhostRobot. Our growing team of 250+ people across the USA and Canada, including entertainment and technology experts from SAG-AFTRA, DGA, IATSE, Teamsters, Amazon, Microsoft, Facebook, and more. Wrapbook is backed by top-tier investors, including Jeffrey Katzenberg’s WndrCo, Andreessen Horowitz, and A* Capital. We have raised $130M and are in a strong financial position.
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 Us
At 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
Our Pledge to Fostering an Inclusive and Safe Workplace:
Wrapbook pledges to be a harassment- and discrimination-free space for everyone, regardless of age, disability, ethnicity, gender identity or expression, nationality, neurotype, personal appearance, political affiliation, professional background, race, religion, or sexual identity or orientation.
Apply Now
Have 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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Skills Required
- 5-8+ years in workers' compensation operations, insurance program management, or related risk management with claims and underwriting exposure
- 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
- Risk management orientation: connect underwriting decisions to claims outcomes and drive loss-reduction initiatives
- Experience using claims and policy data to identify trends, build reports, and recommend operational improvements
- Demonstrated ability to manage vendor and broker relationships with accountability and measurable outcomes
- Excellent communication skills, able to translate WC concepts for non-insurance stakeholders
- Experience with large-deductible or self-insured WC program structures
- 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 PEO risk structures
- ARM, CPCU, or equivalent risk management designation (or in progress)
- Experience with Sedgwick or comparable national TPA platforms
What We Do
Employers in media production and the entertainment industry are constantly hiring. Freelance employees move between projects and could get onboarded 30 or more times in a single year. And yet, much of the industry uses physical paperwork with no easy way to track payments, often struggling with compliance (due to ever-changing laws and union rules), and has few automation processes in place when it comes time to send payroll reports to their accountants. Wrapbook is an intuitive payroll and insurance solution for those balancing multiple projects. With digital solutions, simplified compliance, and comprehensive reporting, we take the stress away so employers and project-based workers can focus on the big picture. Commercial producers, filmmakers, and anyone creating media deserve robust solutions to meet their unique demands. With Wrapbook, you only have to ask for documents from cast and crew once. Our platform lets you move all the onboarding forms associated with any crew from a project to any future ones, giving you back hours. By swapping out paper timecards with digital ones, approving payroll is now a piece of cake. Crew can log into Wrapbook from any device to enter their hours and expenses. Providing producers with the right tools to onboard crew and process payments helps them put routine work on auto-pilot. That way, they can focus on more compelling tasks. Let us tackle paperwork, payroll, and insurance, so you can continue creating the work that matters.
