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Senior Benefits Associate

Senior Benefits Associate

CompanyWayfair
LocationBoston, MA, USA
Salary$Not Provided – $Not Provided
TypeFull-Time
Degrees
Experience LevelSenior

Requirements

  • 3+ years of experience in benefits administration, compliance, or benefits analytics.
  • 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.

Responsibilities

  • 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.
  • 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.

Preferred Qualifications

  • 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.