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Wrapbook logo
Wrapbook

Wrapbook is a smart, intuitive platform that makes production payroll and accounting easier, faster, and more secure.

Senior Benefits Operations Specialist

OperationsOperationsOtherRemoteSeniorTeam 51-200H1B No SponsorCompany SiteLinkedIn

Location

United States

Posted

164 days ago

Salary

$92.5K - $144.4K / year

Seniority

Senior

5 yrs expEnglish

Job Description

Senior Benefits Operations Specialist

Wrapbook

• 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.

Job Requirements

  • 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.

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

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