Benefits Analyst

Be essential at Cars Commerce At Cars Commerce, we’re fanatical about simplifying everything about car buying and selling. We do right by our customers and consumers to better connect the industry with simplified and tierless technology to enhance, measure and drive local automotive retail. Whether through our No.1 most recognized marketplace, , our industry-leading digital experience, Dealer Inspire, our trade and appraisal technology, Accu Trade, our reputation-based digital wholesale auction marketplace, Dealer club, or our new Cars Commerce Media Network, Cars Commerce is essential for success in the automotive industry.

No one ever travels alone here: at its core, Cars Commerce is collaboration. In fact, it’s built into the very fabric of our shared values. We like to say we Rise Together - putting people at the center of what we do, from consumer to customer to community. Life at Cars Commerce makes it easy when we share the ethos to be Open to All, encouraging open-minded communication because we know diverse thinking yields better outcomes.

But critical to our success is Caring to Challenge and Taking Ownership, fueling a competitive spirit in a respectful environment where we think about tomorrow but act today. At our foundation, we have integrity, Doing the Right Thing, even when it’s hard. It’s our shared commitment to these values that makes Cars Commerce a place where growth becomes not only possible, but downright unavoidable.

But don't take our word for it. We are proud to be named one of Built In's 2026 Best Places to Work in Chicago and across the U.S. Ready to make your mark? Join a team that's driving real change in the automotive industry.

The Benefits Analyst is the day-to-day administrator of  U.S. and Canada benefits and leave programs, working within Total Rewards and reporting to the Senior Manager, Benefits. You will keep enrollments, deductions, vendor billing, and leaves accurate and compliant across Workday and our carriers. You will also be the first point of contact for employees, HR Business Partners, Payroll, and vendors on benefits and leave questions.

This role is a strong fit for someone who likes detail, process, and getting people clear answers during sensitive moments such as births, medical events, and open enrollment.

Administer self-funded medical, dental, vision, life, disability, FSA/HSA, commuter, COBRA, and 401(k) programs for U.S. and Canadian employees, including enrollments, qualifying life events, terminations, and eligibility. Configure and maintain benefits setup in Workday and partner with HRIS on releases and testing. Lead the annual open enrollment cycle, including testing, employee support, and follow-up. Generate and process accurate billing and invoices for self-funded health and state leave plans, ensuring compliance with plan parameters and vendor specifications.

Monitor eligibility rules, including benefit eligibility for ACA, and support ACA compliance reporting and temporary-employee guidelines. Support Canadian benefits administration alongside the U.S. programs, including carrier coordination and employee communications. Manage monthly LOA commission calculations, partnering with Payroll to guarantee precise employee payouts and policy compliance. Leverage AI tools and modern technologies to streamline workflows, automate repetitive tasks, and drive operational efficiency.

Champion the adoption of emerging technologies and AI tools to continuously improve team output and efficiency.

Administer all leave programs, including FMLA, parental, caregiver, medical, military, and state paid leave, in partnership with our leave vendor.…