Benefits Operations Specialist

Wrapbook, Inc.

Job Overview

Location

Remote

Job Type

Full-time

Full Job Description

📋 Description

• As a Benefits Operations Specialist at Wrapbook, you will play a critical role in ensuring the smooth and accurate administration of health benefits for production companies using the platform, directly impacting employee well-being and operational reliability in a fast-growing tech-enabled entertainment payroll ecosystem.
• You will manage end-to-end operational workflows including client onboarding and offboarding, data validation, benefits reporting, and third-party coordination, ensuring compliance, accuracy, and timely execution across all benefits-related processes.
• You will partner with Customer Success and enablement teams to build scalable support systems, mentor internal stakeholders, and continuously improve processes to reduce inefficiencies and elevate the client experience.
• Wrapbook is a mission-driven company trusted by industry leaders like SMUGGLER, Tuff, and GhostRobot, backed by top-tier investors including Andreessen Horowitz and WndrCo, and dedicated to transforming production payroll through innovation, inclusivity, and operational excellence.
• In this role, you will develop deep expertise in health benefits administration within the entertainment payroll space, gain exposure to cross-functional tech and operations teams, and position yourself for growth in HR operations, benefits management, or client operations within a high-impact, remote-first environment.

🎯 Requirements

• 3+ years of experience in high-volume operational roles such as fulfillment specialist, operations specialist, benefits advisor, or small group account manager, preferably in tech, health insurance, or disability insurance environments.
• Obsessive attention to detail with proven ability to enter and validate data accurately and efficiently in third-party and proprietary systems, ensuring compliance with benefit eligibility, withholding calculations, caps, and consolidation rules.
• Strong growth mindset and adaptability to thrive in ambiguous, fast-paced environments, with a passion for improving customer experience and reducing operational inefficiencies through proactive process improvements.

🏖️ Benefits

• Unlimited Paid Time Off and the flexibility to work remotely from anywhere in the United States or Canada.
• Comprehensive health and dental benefits, plus up to $1,500 USD/$2,025 CAD for home office IT setup and up to $50 USD/$67.50 CAD monthly for internet/cell phone service.
• Learning and development opportunities, up to 2% RRSP/401K matching, and access to a collaborative, inclusive culture committed to psychological safety and belonging for all employees.

Skills & Technologies

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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