Senior Benefits Operations Specialist
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Job Description
Senior Benefits Operations Specialist for Wrapbook managing benefits operations and process improvements. Collaborating with teams and third-party providers to ensure operational excellence.
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.
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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