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 performanceServe as the primary operational point of contact for our TPA (Sedgwick), managing claim handling expectations, reserving practices, and escalation protocolsMonitor and analyze loss runs, claim frequency/severity trends, and open claim inventory; surface insights to the Sr. Director and drive corrective action with the teamReview large loss and litigated claims on a regular cadence, ensuring the TPA’s handling strategy aligns with program objectivesTrack SLA compliance and claims quality metrics, holding the TPA accountable to performance standardsIdentify patterns in claims data (by state, classification, production type, time of year) and translate findings into actionable recommendations for risk reductionRisk management and WC program administrationDevelop and implement risk mitigation initiatives such as safety programs, return-to-work protocols, and claims management best practices tailored to entertainment industry workflowsUse claims and underwriting data together to identify where operational improvements (better classification, faster reporting, targeted safety guidance) can reduce loss frequency and severityDrive the end-to-end underwriting operations workflow—production company onboarding, classification, state jurisdiction setup, and policy endorsement executionTracking and reporting on Worker Compensation KPIs and SLAs across the WC programTeam leadershipManage, mentor, and develop Workers Compensation Operations and Claims SpecialistsSet clear goals, run regular 1:1s, and drive accountability across all program areas—claims, risk mitigation, underwriting operations, and COI workflowsBalance team workload across the claims and underwriting functions, adjusting capacity allocation as production seasons and claim volumes shiftPartner with the Sr. Director on capacity planning, hiring, and team development as the program scalesAI, knowledge & competitive intelligenceLeverage 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 developmentBuild 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-makingServe as Wrapbook's internal subject matter expert on WC program structures—continuously monitoring the landscape, identifying differentiation gaps, and delivering strategic insights to senior leadershipWhat You'll Have: Required5–8+ years of experience in workers’ compensation operations, insurance program management, or a related risk management function—with exposure across claims and underwriting/policy administration4+ years of people management experience, ideally in a fast-growing or high-volume environmentSolid knowledge of WC claim lifecycles, reserving practices, and TPA performance managementStrong understanding of WC policy structures, classification systems, payroll-based premium calculations, and audit processesA risk management orientation—you naturally connect underwriting decisions to claims outcomes and look for ways to reduce loss frequency and severity across the programExperience using claims and policy data to identify trends, build reports, and recommend operational improvementsDemonstrated ability to manage vendor and broker relationships with a bias toward accountability and measurable outcomesExcellent communication skills with the ability to translate WC concepts for non-insurance stakeholdersPreferred (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 decisionsExperience in entertainment, media, or staffing industry WC programsFamiliarity with employer-of-record (EOR) or professional employer organization (PEO) risk structuresARM, CPCU, or equivalent risk management designation (or in progress)Experience with Sedgwick or comparable national TPA platformsWhy 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 OffWork from anywhere in Canada and USAHealth and Dental benefitsUp to $1,500 USD/ $2,025 CAD towards IT set up for your homeUp to 2% matching RRSP / 401KLearning and Development opportunitiesUp to $50 USD/ $67.50 CAD towards Internet/Cell phone serviceOur 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 NowHave we got your attention? Submit your application today and a member of our Talent team will be in touch with you shortly!

Senior Manager, Risk Operations

Emma

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