Benefits Manager, Retirement and Data

Salary Range: $99,000 - $110,000 per year. The above base pay range may vary depending on location, job-related knowledge, skills and experience. The range listed is just one component of Wayfair’s total compensation package for employees. Depending on the position offered, equity, bonuses, commissions and other forms of compensation may be provided as part of the compensation package, in addition to a comprehensive suite of medical, financial and additional benefits.

Wayfair is based in our Boston, MA office with a hybrid, full-time work schedule;
Monday - Thursday in office and Friday remote.

• 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.

• 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 over payments, eligibility leakage, or administrative errors.

• 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.

• 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, Big Query, etc.) to improve operational transparency.

• 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.

• 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.

• 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, Big Query, or reporting tools preferred.
• High attention to detail with comfort operating in a highly…