Job Description

This position is a hybrid in-office role that works out of our Boston HQ. Monday-Thursday will be working in office and Friday is WFH. This is not a virtual / remote position.

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.

The ideal candidate is an analytical, detail-oriented professional with a strong understanding of health plan design, regulatory compliance, and benefits analytics. This position offers an opportunity to take ownership of complex projects, collaborate with senior stakeholders, and drive cost-effective, consumer driven benefits strategies.

What You'll Do:

Health Plan Administration & Operations

• 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.

Health Plan Analytics & Cost Containment

• 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.

Compliance & Regulatory Oversight

• 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.

Vendor & Stakeholder Collaboration

• 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.

What You'll Need:

• 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.

Massachusetts Applicants: I understand that it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

About Wayfair Inc.

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 [email protected].

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