Senior Manager, Risk Operations

Role Description

Wrapbook is 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.

Qualifications

• 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.

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

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.

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