Director, Risk Management, Workers Compensation & Benefits

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 - Director, Risk Management, Workers Compensation & Benefits - Remote (USA) We’re looking for a strategic, cross-functional leader to own and scale two essential areas of Wrapbook’s business: our Workers Compensation program and our in-house Health Benefits offering. As 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 Concierge service in these domains.On the Workers Compensation side, you’ll lead end-to-end operations including underwriting, claims, compliance, and tooling. You’ll drive the annual WC renewal process, partner with Finance on large-loss forecasting, and shape the long-term Workers Comp strategy—especially as we expand deeper into Film & TV. You’ll also own the evolution of our tooling and customer UI in partnership with Product and Engineering.On the Benefits side, you’ll be the business lead for Wrapbook’s in-house health benefits offering. You’ll be responsible for the strategy, execution, and optimizing the program over time with the support of cross-functional partners. This includes owning the end-to-end customer journey—from enrollment and onboarding through employee deductions and offboarding. You’ll be accountable for scaling service delivery, building relationships with third-party vendors, and delivering regular updates and recommendations to the Executive team on the future evolution of our benefits strategy.This is a strategic and hands-on leadership role that requires deep domain expertise, excellent cross-functional collaboration, and a bias toward execution. You will play a key role in shaping Wrapbook’s Risk and Benefits operations for scale.What you'll Do: Workers’ Compensation Procurement, Renewal & Claims Management LeadershipOwn 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 drive efficient and compassionate claims resolution.Design and implement a customer-first claims experience, focusing on both speed and empathy for injured workers.Drive tooling enhancements in partnership with Product and Engineering to improve automation and user experience—both internal and client-facing.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 claims data and collaborate with third-party administrators to drive efficient claims management, improve outcomes, and inform continuous improvements to insurance program structure and vendor performance.Guide expansion into FTV by optimizing internal and external workflows for scale.Manage operational documentation (claim guides, SOPs, dashboards) and create performance visibility across the team and Senior Leadership teamLeverage data to assess risk trends, recommend safety initiatives, and improve loss outcomes.Benefits Operations & StrategyServe as the business lead for Wrapbook’s in-house health benefits offering for production companies.Build and scale benefits service delivery—including onboarding, off boarding, deductions, eligibility, and reporting—ensuring timely and accurate execution.Partner with third-party vendors, brokers, and carriers to define process, compliance workflows, and operational requirements.Own benefits roadmap and strategic planning, making recommendations to the Executive Team on expansion opportunities and program enhancements.Lead ACA compliance strategy and execution, including eligibility tracking, measurement periods, and generation of 1095-A/B/C reporting.Partner cross-functionally to build scalable workflows to support in-house and external payroll data aggregation across projects and companies.Deliver enablement to internal teams (Sales, CS, Support) on benefits onboarding, eligibility, escalations, and client education.Serve as internal champion for process automation and data integrity in benefits workflows.Leadership, Enablement & Cross-functional ExecutionBuild, manage, and coach a high-performing team of ICs and managers.Drive a strong culture of accountability, documentation, and proactive improvement across all areas of ownership.Collaborate closely with Finance for forecasting, reporting, and financial risk management.Act as a trusted partner to Product and Engineering—bringing operational clarity and customer needs to the forefront of strategic tooling improvements.Create and track KPIs for WC, Claims, and Benefits operations; continuously optimize for scale, efficiency, and service quality.Provide regular updates and strategic input to SLT and Ops leadership.What you'll Have: 10+ years of progressive experience in Workers’ Compensation, Benefits Administration, Risk, or related operations functions.5+ years in a leadership role, with experience managing both ICs and managers.Deep expertise in workers’ comp insurance, including policy procurement, renewals, underwriting, and claims management; entertainment payroll industry experience is preferred, but nor required.Proven track record partnering with Finance and cross-functional teams to forecast workforce volumes, estimate claims exposure, and inform insurance program design and spend.Experience managing insurance vendors, brokers, and TPAs, with a focus on negotiating terms, optimizing policy structure, and driving service-level performance.Strong understanding of ACA-compliant health insurance, measurement/eligibility periods, and multi-employer payroll data aggregation.Demonstrated experience standing up and evolving complex operational programs from scratch.A collaborative operator with exceptional communication skills and a low-ego leadership style.Operationally-minded: you see interdependencies and can lead through ambiguity to build scalable processes.Strong analytical orientation with the ability to partner across Finance and Product on planning and reporting.Experience with third-party systems and vendors (TPAs, carriers, health benefit platforms, etc.).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 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!#LI-Remote

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