Benefits Analyst

Who we are
At CarGurus (NASDAQ: CARG), our mission is to give people the power to reach their destination. We started as a small team of developers determined to bring trust and transparency to car shopping. Since then, our history of innovation and go-to-market acceleration has driven industry-leading growth. In fact, we're the largest and fastest-growing automotive marketplace, and we've been profitable for over 15 years.
What we do
The market is evolving, and we are too, moving the entire automotive journey online and guiding our customers through every step. That includes everything from the sale of an old car to the financing, purchase, and delivery of a new one. Today, tens of millions of consumers visit CarGurus.com each month, and ~30,000 dealerships use our products. But they're not the only ones who love CarGurus-our employees do, too. We have a people-first culture that fosters kindness, collaboration, and innovation, and empowers our Gurus with tools to fuel their career growth. Disrupting a trillion-dollar industry requires fresh and diverse perspectives. Come join us for the ride!
Role overview
We are seeking a Benefits Analyst to be based in our Boston, MA, global headquarters location. 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 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).

What you'll do

• Own day-to-day administration of assigned benefits programs, with a primary focus on leave of absence, disability, and accommodations.
• 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.

The displayed range represents the expected annual base salary / On-Target Earnings (OTE) for this position. On-Target Earnings (OTE) is inclusive of base salary and on-target commission earnings, which applies exclusively to sales roles.
Individual pay within this range is determined by work location and other factors such as job-related skills, experience, and relevant education or training.
This annual base salary forms part of a comprehensive Total Rewards Package. In addition to benefits, this role may qualify for discretionary bonuses/incentives and Restricted Stock Units (RSUs).
Position Pay Range
$72,000 - $91,000 USD
Working at CarGurus
We reward our Gurus' curiosity and passion with best-in-class benefits and compensation, including equity for all employees, both when they start and as they continue to grow with us. Our career development and corporate giving programs, as well as our employee resource groups (ERGs) and communities, help people build connections while making an impact in personally meaningful ways. A flexible hybrid model and robust time off policies encourage work-life balance and individual well-being. Thoughtful perks like daily free lunch, a new car discount, meditation and fitness apps, commuting cost coverage, and more help our people create space for what matters most in their personal and professional lives.
We welcome all
CarGurus strives to be a place to which people can bring the ultimate expression of themselves and their potential-starting with our hiring process. We do not discriminate based on race, color, religion, national origin, age, sex, marital status, ancestry, physical or mental disability, veteran status, gender identity, or sexual orientation. We foster an inclusive environment that values people for their skills, experiences, and unique perspectives. That's why we hope you'll apply even if you don't check every box listed in the job description. We also encourage you to tell your recruiter if you require accommodations to participate in our hiring process due to a disability so we can provide the appropriate support. We want to know what only you can bring to CarGurus. #LI-Hybrid