Senior Manager, Risk Operations

About Us:

Wrapbook is the AI platform for production finance. We’re building a system of action that puts finance teams in control of their whole production, from payroll, to spend, to accounting.

Built for feature films, TV, and commercials, Wrapbook is trusted by teams at Netflix, Paramount, Anonymous Content, and more. With backing from Andreessen Horowitz, Bessemer Venture Partners, and Jeffrey Katzenberg's WndrCo, our team of 350+ is using AI to transform how finance teams work and empower them to do more with less.

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!

#LI-Remote

• Highlight specific experience with Adjust or similar claims platforms and showcase Excel dashboards you built for loss analysis.
• Prepare concrete examples of risk‑mitigation programs you launched and the measurable impact on claim frequency.
• Demonstrate familiarity with entertainment‑industry workflows; cite any production‑finance or crew‑safety projects you’ve supported.
• During interviews, be ready to discuss how you would integrate AI tools like Claude into daily operations to improve efficiency.
• Emphasize leadership style: give examples of how you coached team members and balanced workload during peak production seasons.
• Research Wrapbook’s AI‑driven product suite beforehand so you can speak intelligently about how risk operations fit within the broader platform.
• Ask about the TPA relationship and KPI expectations to show you understand the operational nuances of the role.