Senior Benefits Analyst

Wayfair•Boston, MA

3d•Hybrid

About The Position

This position is based in our Boston, MA, office with a hybrid, fulltime, work schedule; Monday - Thursday in office and Friday remote. The Senior Benefits Analyst is a critical individual contributor responsible for the technical integrity, operational reliability, and analytical rigor of the Company's benefits ecosystem. This role sits at the intersection of benefits strategy, HR systems, and data, ensuring accurate system integrations, stable downstream processing, and high-quality insights that support benefit design, compliance, cost management, and population health outcomes. The Senior Benefits Analyst partners closely with HRIS, Payroll, Finance, and external vendors to proactively monitor integration health, troubleshoot complex system issues, configure Workday Time Off programs, and transform benefits data into actionable intelligence.

Requirements

3+ years of experience within Employee Benefit administration.
Bachelor's degree in Human Resources, business, or related field preferred - equivalent experience and proven results in HR Management or Benefits will also be strongly considered.
Ability to build productive relationships and influence cross-functional and vendor partners.
Ability to effectively manage timelines, delivery, and communication across teams.
Ability to manage complex projects and work autonomously.
Service orientation with a consultative lens.
Comfortable adapting to change in a fast-paced, dynamic and ambiguous environment.

Nice To Haves

Experience working with Workday, Alight CBA, Artemis a plus.

Responsibilities

Monitor end-to-end benefits system integrations across Workday, payroll, carriers, and third-party administrators, including eligibility, enrollment, contributions, and demographic data.
Design, document, and maintain integration logic, file specifications, data mappings, and downstream dependencies.
Establish and execute integration health monitoring, including reconciliations, error tracking, variance analysis, and root-cause investigation.
Proactively identify integration risks and data anomalies; lead issue resolution through cross-functional collaboration and vendor escalation.
Partner with HRIS and vendors to test and validate integrations for new plans, plan year changes, acquisitions, and system enhancements.
Configure and maintain Workday Time Off plans, accruals, eligibility rules, and carryover logic, including country- and population-specific variations.
Support audits, testing cycles, and troubleshooting related to time off balances, accrual calculations, and payroll impacts; maintain clear configuration documentation and SOPs.
Perform detailed benefits data analysis, including enrollment trends, contribution behavior, utilization patterns, and financial impacts.
Clean, normalize, and reconcile data across systems to ensure accuracy, consistency, and reliability for reporting, modeling, and decision-making.
Analyze population health data to identify utilization drivers, cost trends, and opportunities to improve program effectiveness and outcomes.
Translate complex data into actionable insights for benefits leadership; support vendor performance management, compliance reviews, and continuous process improvement.