Director, Risk Management, Workers Compensation & Benefits

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