Senior 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 - Senior Benefits Operations Specialist (Remote - USA)

We are seeking a Senior Benefits Operations Specialist to play a critical role in scaling and optimizing Wrapbook’s health benefits offering for production companies. In this senior-level individual contributor role, you will own complex operational workflows, serve as a subject matter expert for our benefits programs, and act as a key partner across Customer Success, Sales, Enablement, Product, and third-party benefits providers.

You will not only execute core benefits operations, but also lead process improvements, handle escalations, mentor junior team members, and help shape the future state of our benefits operations as the program evolves.

What you'll do:

• Own and execute end-to-end benefits operations including onboarding, off boarding, eligibility management, contribution adjustments, reconciliations, and reporting.

• Manage complex or non-standard benefits scenarios, including eligibility edge cases, retroactive changes, multi-project consolidations, and escalations.

• Ensure benefits data is entered accurately, completely, and on time to support compliant withholdings and reporting.

• Serve as a primary point of contact for third-party benefits providers, ensuring accurate and timely data exchange and issue resolution.

• Oversee and validate weekly and ad hoc reports sent to third-party benefits providers.

• Conduct detailed audit reviews to ensure:

  • Accurate calculation of benefit withholdings, caps, and consolidations across projects

  • Correct capture of benefit eligibility and enrollment status

  • Alignment between internal systems and external provider records

• Identify trends or recurring discrepancies and drive corrective actions.

• Handle advanced customer inquiries and escalations via phone and email with professionalism and subject matter expertise.

• Translate recurring issues and learnings into process documentation, FAQs, and training materials.

• Partner closely with Enablement to upskill Customer Success, Sales and other internal teams on benefits workflows and policies.

• Proactively identify opportunities to improve benefits operations, systems, and customer experience.

• Lead or support process redesign efforts as the benefits program evolves, including documenting SOPs and implementing scalable solutions.

• Provide feedback and recommendations to Product and Operations leadership based on operational insights and customer impact.

• Act as a mentor and knowledge resource for Benefits Operations Specialists and adjacent team members.

• Support onboarding and training of new hires within Benefits Operations.

• Partner cross-functionally with Customer Success, Payroll Operations, Product, and Legal/Compliance to ensure alignment and operational excellence.

What you'll have:

• 5+ years of experience in high-volume, operational roles such as Benefit Operations, Small group or employee benefits administration, operations specialist or benefits advisor roles (Tech, payroll, or health insurance experience strongly preferred)

• Deep understanding of benefits administration workflows, eligibility rules, and contribution calculations.

• Demonstrated ability to own complex processes independently and solve ambiguous problems.

• Strong analytical skills with exceptional attention to detail and accuracy.

• Experience working in fast-paced, evolving environments with changing requirements.

• Proven ability to communicate clearly and confidently with customers, vendors, and internal stakeholders.

• Experience with data entry and reconciliation in both proprietary and third-party systems.

• Entertainment payroll experience is a strong plus but not required.

Why Join Us

At Wrapbook, creativity meets technology — and not just in the product.

In addition to a competitive salary and all the benefits you can expect from a fast-growing technology company, you’ll get access to a team of creative problem solvers and the chance to see your contributions make large impacts. Benefits include:

• 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.

Apply Now

Have we got your attention? Submit your application today and a member of our Talent team will be in touch with you shortly!

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