Benefits Analyst

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, Cars.com, our industry-leading digital experience, Dealer Inspire, our trade and appraisal technology, AccuTrade, our reputation-based digital wholesale auction marketplace, Dealerclub, 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 Cars.com 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.

Benefits administration

• →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 heath 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.

Leave of absence administration

• →Administer all leave programs, including FMLA, parental, caregiver, medical, military, and state paid leave, in partnership with our leave vendor.
• →Partner with HR Business Partners, Payroll, and Legal on leave cases and employee questions.

Vendor and financial management

• →Serve as day-to-day contact for carriers, vendors, and the benefits consultant.
• →Manage recurring vendor invoicing and funding approvals, and reconcile billing discrepancies.
• →Support annual renewals and vendor contract timelines.

Reporting and compliance

• →Pull and analyze benefits data, such as employer contribution reports, enrollment counts, and leave metrics, for Total Rewards leadership and Finance.
• →Support the 401(k) administration, annual audit, and investment committee.
• →Maintain process documentation.
• →Answer employee, HRBP, and manager questions with accuracy and discretion, protecting confidential medical and personal information.

Intranet content and communications calendar

• →Own and refresh benefits and leave content on the intranet, keeping it accurate, concise, and consistent in tone and structure.
• →Build and maintain a benefits communications calendar covering open enrollment, new-hire and life-event reminders, vendor programs, and policy changes.
• →Partner with the Internal Communications team to draft, review, and schedule employee emails, FAQs, benefits guides, and webinars.
• →Coordinate with vendors on co-branded or vendor-provided materials, and confirm that messaging matches plan details and U.S. and Canada differences before release.

• Bachelor's degree in Human Resources, Business, or a related field, or equivalent experience.
• 3–6 years of experience administering employee benefits and/or leaves of absence.
• Working knowledge of FMLA, ACA, COBRA, ERISA basics, and state paid leave and paid sick requirements. Continuously monitor, interpret, and maintain compliance with evolving federal, state, and local statutory leave laws and sick leave mandates. 
• Hands-on experience with an HRIS, with benefits configuration experience in Workday strongly preferred.
• Strong analytical skills and advanced Excel or Google Sheets skills, including lookups, pivots, and data reconciliation.
• Excellent attention to detail and the ability to manage recurring deadlines, such as payroll cutoffs, invoice approvals, and enrollment windows.
• Clear written and verbal communication, with a service mindset and sound judgment handling confidential information.
• Ability to work with multiple vendors, Payroll, HRBPs, and Legal at once.
• Demonstrated curiosity and proficiency in using AI tools (e.g., Gemini, Claude, Copilot or role-specific AI platforms) to boost personal and team productivity. 
• Forward-thinking mindset with an eagerness to explore, evaluate, and adopt AI capabilities to refine business processes. 

• Experience with U.S. and Canadian benefits, including group health, RRSP, or Canadian leave requirements.
• Experience with leave vendor platforms and benefits consultants or brokers.
• Experience supporting open enrollment, including employee communications.
• Professional certification such as PHR, SHRM-CP, CEBS, or CLMS.

Tools and systems: Workday (Benefits and Absence), Google Workspace, Microsoft Office