This position is based in our Boston, MA, office with a hybrid, fulltime, work schedule; Monday - Thursday in office and Friday remote.
Wayfair is seeking a technically rigorous and strategically minded Benefits Manager to own the operational, financial, and compliance backbone of our global benefits programs. This role serves as the systems architect and fiduciary steward of our health, welfare, and retirement infrastructure across the U.S., Canada, U.K., Ireland, and other global markets.
You will be responsible for ensuring that benefits programs operate as designed - with data integrity, financial discipline, regulatory compliance, and scalable process efficiency. This role directly protects the company from financial leakage, operational risk, and fiduciary exposure while strengthening the employee experience. You will manage one Benefits Associate and set the operational standards that govern vendor accountability, system accuracy, and global retirement oversight.
What You'll Do- Benefits Infrastructure & Systems Ownership - Serve as functional owner of the global benefits data ecosystem, including Workday integrations, vendor eligibility feeds, payroll deductions, and financial reconciliation processes.
- Design and maintain integration logic, validation controls, and reconciliation routines to ensure 100% accuracy in enrollment, eligibility, and payroll data.
- Identify systemic risk in vendor operations and data flows; lead remediation efforts across HRIS, Payroll, Finance, and external administrators.
- Establish operational KPIs and reporting frameworks to monitor vendor performance and internal processing accuracy.
Financial Stewardship & Cost Governance - Own the end-to-end financial lifecycle of global benefits programs, including PO management, invoice reconciliation, accrual validation, and expense forecasting.
- Partner with Finance to model benefit cost trends and provide executive-level reporting on plan performance and cost drivers.
- Identify cost-containment opportunities without compromising employee value proposition.
- Ensure financial controls are in place to prevent overpayments, eligibility leakage, or administrative errors.
Global Retirement Strategy & Fiduciary Oversight - Lead administration and governance of retirement programs including:
- U.S. 401(k)
- Canada DPSP/RRSP
- U.K. pension schemes
- Ireland retirement plans
- Serve as primary operational liaison to recordkeepers, auditors, and Retirement Committee stakeholders.
- Execute annual 401(k) audit, Form 5500 filings, nondiscrimination testing, and related compliance activities.
- Monitor plan design competitiveness and regulatory developments across jurisdictions.
- Partner with consultants and committee members to uphold fiduciary best practices and mitigate regulatory risk.
Process Optimization & Automation - Identify manual, error-prone workflows and implement automation and control enhancements.
- Build scalable SOPs and documentation to support lean team operations.
- Lead testing and stabilization activities for system enhancements, plan year changes, and vendor transitions.
- Create data dashboards and reporting tools (Excel, Looker, BigQuery, etc.) to improve operational transparency.
Compliance & Risk Management - Ensure adherence to regulatory frameworks including ERISA, ACA, COBRA, and applicable international pension regulations.
- Maintain audit-ready documentation and internal controls.
- Partner with Legal and external advisors on compliance reviews and regulatory changes.
- Proactively identify compliance gaps and design mitigation strategies.
Team Leadership & Operational Excellence - Directly manage one Benefits Associate, providing clear prioritization, technical guidance, and professional development.
- Establish a culture of precision, accountability, and continuous improvement.
- Serve as escalation point for complex benefits or financial issues.
- Drive a high-performance operating model within a lean team structure.
What You'll Need- - 5+ years of experience in benefits administration, HR operations, or total rewards.
- Direct experience managing retirement plans and U.S. 401(k) audit processes.
- Strong financial acumen with experience reconciling vendor invoices, managing budgets, and analyzing benefit costs.
- Demonstrated expertise in benefits data integrations and HRIS systems (Workday strongly preferred).
- Proven ability to identify systemic risk, conduct root cause analysis, and implement sustainable solutions.
- Advanced Excel skills; experience with SQL, BigQuery, or reporting tools preferred.
- High attention to detail with comfort operating in a highly regulated environment.
Preferred
- Bachelor's degree in HR, Finance, Business, or related field.
- Experience supporting global benefit programs.
- Familiarity with fiduciary governance and Retirement Committee operations.
- Experience working in a lean, high-growth environment.
Assistance for Individuals with DisabilitiesWayfair 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 Accomodations for Applicants form .
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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.
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