Associate People Operations Specialist

<div class="content-intro"><p><strong>Who we are</strong></p> <p>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.</p> <p><strong>What we do</strong></p> <p>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!</p></div><p><strong>Role overview</strong></p> <p>The Associate People Operations Specialist provides administrative and operational support across benefits, payroll, HR systems, and employee lifecycle processes. This role is critical to delivering accurate, compliant, and high-quality People Operations support while enhancing the overall employee experience.</p> <p>The role focuses on executing established workflows, maintaining employee and benefits data, managing vendor coordination, and responding to employee queries. The ideal candidate is detail-oriented, technically proficient, and capable of managing multiple priorities across global programs.</p> <p><strong>What you'll do</strong></p> <h4><strong>Benefits Administration &amp; Vendor Management</strong></h4> <ul> <li>Manage global benefits operations across the US, Canada, UK, and Ireland, overseeing benefit administration, invoice tracking, and the processing and reconciliation of payments across approximately 20 vendors (including medical, dental, and life insurance)</li> <li>Conduct monthly audits of benefit plans, identifying discrepancies and driving resolution</li> <li>Administer global pension and retirement schemes (UK, Ireland, US), including system uploads and quarterly fee tracking</li> <li>Oversee FSA/HSA funding aligned with payroll cycles, including quarterly employer contributions</li> <li>Administer COBRA processes and maintain associated tracking documentation</li> <li>Manage Evidence of Insurability (EOI) approvals and send foll