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Wrapbook · 2 days ago

Senior Benefits Operations Specialist

United States

Full-time

Remote

Senior Level

$92K/yr - $144K/yr

5+ years exp

Wrapbook is a smart platform that simplifies production payroll and accounting for production companies. They are seeking a Senior Benefits Operations Specialist to manage and optimize their health benefits offerings, execute operational workflows, and partner with teams across the company to enhance benefits operations.

Computer Software

Growth Opportunities

Responsibilities

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

Qualification

Benefits administrationOperational workflowsData entryReconciliationAnalytical skillsCustomer communicationProcess improvementMentoringTeam collaborationAttention to detail

Required

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

Preferred

Entertainment payroll experience is a strong plus but not required

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

Company

Wrapbook

Glassdoor4.5

Wrapbook is the next standard in production payroll and accounting—a force multiplier that empowers finance teams in film, TV, commercials, and other media to accomplish more, faster, with greater data integrity.

Founded in 2018

New York, US

51-200 employees