Senior Benefits Associate, Wayfair

• The ideal candidate is an analytical, detail-oriented professional with a strong understanding of health plan design, regulatory compliance, and benefits analytics
• 3+ years of experience in benefits administration, compliance, or benefits analytics
• Bachelor’s degree in Human Resources Management or related field preferred - equivalent experience and proven results in HR Management, Benefits, FMLA, ADA will also be strongly considered
• Strong knowledge of U.S. and/or Canadian benefits regulations (ACA, ERISA, HIPAA, COBRA, provincial healthcare laws, etc.)
• Experience with health plan data analysis, claims reporting, and cost containment strategies
• Strong problem-solving skills with the ability to interpret complex data and make strategic recommendations
• Ability to work independently in a fast-paced team environment while managing multiple priorities
• Experience working with HRIS systems and benefits platforms (Workday / Alight preferred)
• Excellent communication and stakeholder management skills

• We are seeking a Senior Benefits Associate to support the administration, compliance, and cost management of our North American health and welfare programs
• This role will play a critical part in ensuring compliance with federal, state, and provincial regulations, analyzing key cost drivers, and implementing strategic interventions to optimize healthcare spend
• This position offers an opportunity to take ownership of complex projects, collaborate with senior stakeholders, and drive cost-effective, consumer driven benefits strategies
• Support the administration of U.S. and Canadian health & welfare plans, ensuring compliance, efficiency, and a seamless employee experience
• Act as a subject matter expert for escalated benefits issues, partnering with vendors and internal teams to drive resolution
• Lead annual benefits enrollment efforts, including communication strategies, vendor system testing, and employee education initiatives
• Conduct in-depth analyses of claims data, plan performance, and utilization trends to guide program enhancements
• Analyze health plan cost drivers, including claims trends, high-cost claimants, and utilization patterns
• Develop and present data-driven recommendations to optimize plan design, reduce unnecessary costs, and enhance employee engagement
• Support negotiations with vendors and insurers to ensure cost-effective benefits solutions
• Stay informed on industry benchmarks, regulatory changes, and emerging trends to proactively manage risks and opportunities
• Ensure ongoing compliance with ERISA, ACA, HIPAA, COBRA, and state-specific regulations
• Lead efforts on 5500 filings, PCORI, RxDC and other mandated reporting
• Partner with legal and external counsel to stay ahead of regulatory updates affecting U.S. and Canadian benefits programs
• Manage vendor relationships, ensuring adherence to contracted service levels, reporting accuracy, and cost containment goals
• Support RFPs, plan renewals, and implementation of new benefits programs
• Collaborate cross-functionally with Talent, Finance, Legal, and Procurement teams to align benefits programs with business needs
• Provide strategic insights and recommendations to senior leadership on benefits trends and plan performance

Wayfair emerged in the early era of eCommerce with a mission to revolutionize online shopping, offering customers a convenient platform to purchase goods. Today, it stands as one of the foremost global players in the online furniture delivery industry, boasting an impressive inventory of over 33 million products.