Benefits Associate

We are seeking a detail-oriented and employee-focused Benefits Associate to support the administration of Wayfair’s U.S. health and welfare programs. This role will serve as the primary day-to-day liaison between Wayfair’s Benefits team and our benefits third party administrator, ensuring employee issues are accurately triaged, escalated, and resolved.

This position plays a critical role in protecting the employee experience by identifying breakdowns in vendor execution, driving timely remediation, and ensuring benefits programs operate as designed. This role is central to ensuring that Wayfair’s benefits programs function as intended—especially when vendor execution falls short. By serving as the connective tissue between employees, vendors, and internal partners, this role directly protects the employee experience, mitigates operational risk, and strengthens vendor accountability.

What You’ll Do

Benefits Administration

• Serve as the primary point of contact between Wayfair’s Benefits team to third party administrators & record keepers for day-to-day benefits administration issues across health and welfare programs. Escalating the Benefits Manager for support as needed.
• Triage employee benefit issues resulting from vendor errors, system limitations, or process gaps, ensuring accurate diagnosis and resolution.
• Review and validate third party administrator’s handling of enrollments, eligibility, deductions and coverage to ensure alignment with plan design and Wayfair policy.
• Administer the Benefits escalation process from intake through resolution, partnering with our third party administrator, carriers, payroll, and internal stakeholders as needed.
• Translate complex or technical vendor issues into clear explanations for employees and internal partners.

Vendor Management & Accountability

• Actively monitor our third party administrator’s operational performance, identifying recurring issues, error trends, and systemic risks across health and welfare administration.
• Partner with senior Benefits team members to support root-cause analysis and process improvements.
• Support implementation and stabilization activities related to vendor changes, enhancements, or remediation efforts.

Employee Experience & Support

• Provide high-touch, empathetic support to employees experiencing benefits plan issues, particularly those with coverage gaps or financial impact.
• Ensure employee inquiries are resolved accurately and efficiently, even when resolution requires multi-step vendor intervention.
• Support onboarding and open enrollment by ensuring vendor systems function as intended and issues are addressed quickly.

Open Enrollment & Program Support

• Support annual open enrollment activities, including system testing, employee support, and issue triage.
• Validate employee-facing materials and system outputs for accuracy and consistency.
• Assist with benefits program updates, renewals, and operational readiness.

Compliance & Documentation

• Assist with compliance-related activities tied to health and welfare programs  (e.g., ACA, ERISA, COBRA).
• Maintain internal documentation, issue logs, and standard operating procedures related to vendor administration.
• Support data gathering for audits, reporting, and internal reviews.

What You'll Need

• 2+ years of experience in benefits administration, HR operations, or a related role.
• Experience supporting a third-party benefits administrator in an operational or issue-resolution capacity.
• Working knowledge of U.S. health and welfare benefits.
• Demonstrated ability to triage issues, identify root causes, and drive resolution across multiple parties.
• High attention to detail, strong follow-through, and comfort managing sensitive employee matters.
• Experience working with HRIS and benefits administration platforms (Workday and/or Alight strongly preferred).

Preferred

• Bachelor’s degree in Human Resources, Business Administration, or a related field.
• Experience supporting open enrollment or retirement plan operations.
• Familiarity with compliance concepts (e.g., contribution limits, eligibility rules, nondiscrimination testing).
• Strong Excel or Google Sheets skills for tracking issues, reconciliations, and trends.