Benefits Operations Specialist
WrapbookRemotePosted 16 March 2026
Job Description
Benefits Operations Specialist
About Us:
Wrapbook is a smart, intuitive platform that makes production payroll and accounting easier, faster, and more secure. We provide a unified payroll platform that seamlessly connects your entire team—production, accounting, cast, and crew—all in one place. Wrapbook empowers production teams to manage projects, pay cast and crew, track expenses, and generate data-driven insights, while enabling workers to manage timecards, track pay, and onboard to new projects from any device. Wrapbook brings clarity and dependability to production payroll, while increasing the productivity of your whole team.
Trusted by companies of all sizes, Wrapbook powers payroll for some of the industry’s top production companies, including SMUGGLER, Tuff, and GhostRobot. Our growing team of 250+ people across the USA and Canada, including entertainment and technology experts from SAG-AFTRA, DGA, IATSE, Teamsters, Amazon, Microsoft, Facebook, and more. Wrapbook is backed by top-tier investors, including Jeffrey Katzenberg’s WndrCo, Andreessen Horowitz, and A* Capital. We have raised $130M and are in a strong financial position.
The Opportunity - Benefits Operations Specialist (Remote - USA / Canada)
We are looking for a Benefits Operations Specialist to play an essential role in supporting our health benefits offering for production companies using Wrapbook. In this role you will be responsible for all of the operational aspects associated with our medical benefits offering including: onboarding, off boarding, reporting, customer support and third party referrals. The ideal candidate will be able to adjust and update processes based on the evolution of the program. You are comfortable working in an ever evolving client-service environment and are comfortable communicating cross-functionally and directly to clients and third parties.
What You'll Do:
- Support operational aspects necessary for a health benefits offering including onboarding, offboarding, reporting, contribution adjustments and more.
- Responsible for ensuring data provided by our customers is entered correctly and on time in our system to ensure we withhold and report accurately
- Offboard employees in our systems as we receive updates from our customers about medical benefits changes for their employees
- Provide reports to customers and third party benefits providers
- Monitor and respond appropriately to customer inquiries via phone or email. Partner with enablement to enable internal teams to eventually field rudimentary questions.
- Support onboarding of clients that choose our health benefits program. Mentor Customer Success to eventually be able to lead customer onboarding themselves.
- Exceed service level objectives on accurate and timely reporting, case resolution and the percentage of medical benefit adjustments.
- Proactively share new ways to enhance the product, process or systems
- Review various audit reports ensuring we are:
- Calculating withholdings accurately including dollar amounts, caps and consolidation across projects.
- Capturing benefit eligibility correctly
What You'll Have:
- 3+ years experience in high-volume operational roles (fulfillment specialist, small group account manager, operations specialist, benefits advisor, etc.), preferably in the tech, health insurance, or disability insurance
- Growth mindset – thrives in an ambiguous, fast-paced environment
- Obsessively organized and detail-oriented
- Approach problems with a passion for improving the customer experience and reducing operational inefficiencies
- Experience within the entertainment payroll industry is preferred but not required.
- Strong attention to detail; work accurately and at a reasonable rate of speed;
- Experience with data entry in third party and proprietary software
- Nice to have: Entertainment Payroll Experience
Why Join Us
At Wrapbook, creativity meets technology — and not just in the product.
In addition to a com ... (truncated, view full listing at source)
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