Director, Risk Management, Workers Compensation & Benefits

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Wrapbook

📍Remote - Worldwide

Summary

Join Wrapbook as the Director, Risk Management, Workers Compensation & Benefits and lead the strategic scaling of Workers' Compensation and in-house Health Benefits. You will define the vision, build and evolve operational models, and lead teams delivering concierge service in these areas. For Workers' Compensation, you'll manage end-to-end operations, including underwriting, claims, compliance, and tooling; drive annual renewals; partner with Finance on forecasting; and shape long-term strategy. For Benefits, you'll lead the in-house health benefits offering, managing strategy, execution, and optimization, including the customer journey from enrollment to offboarding. This role demands deep domain expertise, cross-functional collaboration, and a bias toward execution, playing a key role in shaping Wrapbook's Risk and Benefits operations for scale. You will build, manage, and coach a high-performing team, fostering a culture of accountability and proactive improvement. You will also collaborate extensively with other departments and provide regular updates to senior leadership.

Requirements

  • 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.)

Responsibilities

  • Own 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 team
  • Leverage data to assess risk trends, recommend safety initiatives, and improve loss outcomes
  • Serve 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
  • Build, 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

Benefits

  • 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

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