Role overview

We are seeking a Benefits Analyst to be based in our Boston, MA, global headquarters location, on a hybrid schedule. This role will be reporting to the Director of Benefits and will be responsible for the oversight and administration of several CarGurus’ North America Benefits programs and perks as well as heavy involvement in new initiatives. This role will collaborate closely with both internal and external stakeholders and partners to optimize benefits offerings and provide excellent service to employees.

What you’ll do 

• Be involved with most areas of employee benefits in partnership with team members.
• Own day-to-day administration of assigned benefits programs, with 50% focus on leave of absence, disability, and accommodations to start.
• Manage leave and accommodation cases end-to-end, partnering with vendors to ensure timely and accurate execution, and clear collaboration and communication with HR Strategy Partners, claimant employee and their manager.
• Provide guidance and education to employees and managers; act as a subject matter expert on benefits programs.
• Monitor vendor performance, data, and reporting; identify issues and hold partners accountable to service levels.
• Collaborate cross-functionally (People Operations, People Applications (HRIS), Payroll, Legal, vendors) to ensure smooth program delivery.
• Maintain confidentiality while ensuring compliance with legal and company requirements.
• Support audits, reporting, and analysis; identify trends and recommend improvements.
• Contribute to projects and program enhancements, vendor RFPs, and key initiatives like Annual Open Enrollment.
• Partner with the Benefits team to meet priorities and escalate when needed.
• Create employee communications for assigned programs.
• Maintain ~60% onsite presence, with flexibility during peak periods.

What You’ll Bring

• 5+ years of U.S. benefits experience, preferably in fast paced, growing tech environments.
• Experience in most functions of employee benefits administration including health and welfare, well-being, life and disability, leaves, 401(k), and voluntary plans. Time off, leaves and accommodations administration experience, as well as a passion for well-being are a plus.
• Proven examples of independently owning several areas of benefits responsibilities, including careful tracking, accountability and clear communication with all critical stakeholders a must.
• Examples of working collaboratively in a team environment.
• Affinity for educating and communicating on employee benefits, including presenting to audiences.
• Appreciation for compliance and risk reduction with comfort in and knowledge of local, state and federal employee benefits regulations, such as ERISA, IRS, DOL, ACA, HIPAA, and COBRA.
• Examples of successfully completing special projects on top of normal day to day responsibilities.
• High level of integrity and discretion when handling sensitive employee information.
• Robust analytical skills, with the ability to interpret data and make data-driven recommendations.
• Attention to detail and accuracy.
• Comfort and proficiency with computer software and HRIS systems (Google products and Workday experience a plus).