Senior Manager, Risk Operations

Wrapbook, Inc.

Job Overview

Location

Remote - US & Canada

Job Type

Full-time

Full Job Description

📋 Description

• Lead the full lifecycle of Wrapbook’s Workers’ Compensation program, including claims oversight, risk mitigation, underwriting operations, and day-to-day administration for tens of thousands of project workers across hundreds of entertainment productions.
• Serve as the primary operational point of contact for the Third-Party Administrator (Sedgwick), managing claim handling expectations, reserving practices, escalation protocols, and SLA compliance.
• Monitor and analyze loss runs, claim frequency/severity trends, and open claim inventory to surface actionable insights and drive corrective actions with the team.
• Review large loss and litigated claims on a regular cadence to ensure TPA handling strategies align with program objectives and risk mitigation goals.
• Track and report on Workers’ Compensation KPIs and SLAs across claims, underwriting, and COI workflows, holding vendors accountable to performance standards.
• Identify patterns in claims data by state, job classification, production type, and seasonality to develop targeted risk reduction initiatives.
• Design and implement risk mitigation programs including safety protocols, return-to-work strategies, and classification best practices tailored to entertainment industry workflows.
• Drive end-to-end underwriting operations: onboarding production companies, setting up state jurisdictions, assigning correct classifications, and executing policy endorsements.
• Manage, mentor, and develop a team of Workers’ Compensation Operations and Claims Specialists, setting clear goals, conducting 1:1s, and balancing workload across claims and underwriting functions.
• Partner with the Senior Director on capacity planning, hiring, and team development as the WC program scales with company growth.
• Leverage AI tools (including Claude, Dust, and emerging platforms) to automate research, draft documentation, streamline workflows, and enhance team productivity.
• Build and maintain a centralized Workers’ Compensation knowledge base and collaborate with AI Champions to deploy self-serve AI agents that reduce friction for internal teams.
• Act as Wrapbook’s internal subject matter expert on WC program structures, continuously monitoring industry trends, identifying competitive differentiators, and delivering strategic insights to senior leadership.
• Translate complex WC concepts into clear, actionable guidance for non-insurance stakeholders across production, accounting, and engineering teams.
• Use claims and underwriting data together to identify operational improvements—such as faster reporting, better classification accuracy, and targeted safety interventions—that reduce loss frequency and severity.
• Ensure compliance with state-specific WC regulations and coordinate with brokers and carriers on policy renewals, audits, and premium calculations based on payroll data.
• Maintain accurate records of all WC-related documentation, including certificates of insurance (COIs), policy endorsements, and audit results.
• Support the broader Risk & Benefits Operations division by contributing expertise to Benefit Operations, Unemployment Insurance, and Company Insurance programs as needed.

🎯 Requirements

• 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—naturally connecting underwriting decisions to claims outcomes and seeking ways to reduce loss frequency and severity
• Demonstrated ability to manage vendor and broker relationships with a bias toward accountability and measurable outcomes

🏖️ 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

Skills & Technologies

Senior

Remote

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Wrapbook, Inc.

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About Wrapbook, Inc.

Wrapbook builds cloud-based payroll, onboarding, insurance and compliance software for the entertainment industry. The platform automates timecards, union reporting, tax withholding, residual payments and workers’ comp while providing digital start-work packets and e-signatures. Production accountants, studios, ad agencies and unions use the service to manage cast and crew across film, television, commercials and live events, integrating with accounting packages and banking APIs for real-time cost tracking.

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