Benefits Associate

Wayfair Benefits Associate This position is based in our Boston, MA, office with a hybrid, fulltime, work schedule; Monday - Thursday in office and Friday remote. 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 intendedespecially 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 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. Wayfair is fully committed to providing equal opportunities for all individuals, including individuals with disabilities. As part of this commitment, Wayfair will make reasonable accommodations to the known physical or mental limitations of qualified individuals with disabilities, unless doing so would impose an undue hardship on business operations. If you require a reasonable accommodation to participate in the job application or interview process, please let us know by completing our Accommodations for Applicants form. Wayfair is one of the world's largest online destinations for the home. Whether you work in our global headquarters in Boston, or in our warehouses or offices throughout the world, we're reinventing the way people shop for their homes. Through our commitment to industry-leading technology and creative problem-solving, we are confident that Wayfair will be home to the most rewarding work of your career. If you're looking for rapid growth, constant learning, and dynamic challenges, then you'll find that amazing career opportunities are knocking. No matter who you are, Wayfair is a place you can call home. We're a community of innovators, risk-takers, and trailblazers who celebrate our differences, and know that our unique perspectives make us stronger, smarter, and well-positioned for success. We value and rely on the collective voices of our employees, customers, community, and suppliers to help guide us as we build a better Wayfair and world for all. Every voice, every perspective matters. That's why we're proud to be an equal opportunity employer. We do not discriminate on the basis of race, color, ethnicity, ancestry, religion, sex, national origin, sexual orientation, age, citizenship status, marital status, disability, gender identity, gender expression, veteran status, genetic information, or any other legally protected characteristic. Your personal data is processed in accordance with our Candidate Privacy Notice. If you have any questions or wish to exercise your rights under applicable privacy and data protection laws, please contact us at .

Created: 2026-03-05