"Alerted.org

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.

What You'll Do

+ 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.

+ Groups Served: North America.

What You'll Need

+ 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.

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

Assistance for Individuals with Disabilities

Wayfair 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 (https://docs.google.com/forms/d/1ElBqKaQYGR9j0NiQHQYCGbHkqKqN746Nk62pI32IyLU) .

Need Technical Assistance?

For more information about applying for a career at wayfair, visit our FAQ page here (https://www.aboutwayfair.com/careers/careers-faq) .

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 (https://www.wayfair.com/careers/privacy). If you have any questions or wish to exercise your rights under applicable privacy and data protection laws, please contact us at [email protected].