Benefits Analyst at Cars Commerce, Chicago, IL

Benefits Analyst at Cars Commerce in Chicago, IL. Full-time. $64,600 to $79,150 a year. Apply with swipeandhired.

Power confident decisions at Cars.com
Cars.com is the marketplace millions of people trust to buy and sell cars with confidence.

More than 25 years ago, we started as a simple idea, connect buyers and sellers, and today we do a lot more: trusted reviews, transparent pricing, and real-time, proprietary data that cut through the noise of one of life's biggest purchases. Our scaled marketplace, paired with interconnected technology, data, and media, gives dealers and OEMs everything they need to sell more cars.

At Cars.com, we debate openly, decide fast, and deliver what we say we will. We solve real problems for car shoppers and dealers, simplify for speed, and focus on what matters most. We win together or not at all. Here, your work counts, your ideas can help shape what’s next, and you’ll build alongside people who have your back.

We’re in the middle of a real transformation, modernizing the company and investing in AI and data to move faster. You're joining the No. 1 brand people think of first when shopping for a car, at the exact moment it's being rebuilt for what's next. You help decide what that becomes. That kind of influence is rare, and it's exactly why this is a place worth building your career.

Don't just take our word for it, we're proud to be named one of Built In's 2026 Best Places to Work in Chicago and across the U.S.

Ready to help build the most trusted place to buy and sell a car? Join us.

Position Summary
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.

Key Responsibilities
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.

Required Qualifications

• 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.

Preferred Qualifications

• 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
Compensation

We share compensation up front so you have the information you need to make a confident decision. This range reflects target base compensation. Where you land depends on skills and experience. If this range works for you, we encourage you to apply.

Salary Range: $64,600.00-79,150.00
Benefits
Confidence, built in. The same confidence we build for car buyers and sellers, we build into how we treat our own:

• Medical, dental & vision from day one — no waiting period
• 401(k) with company match, immediate vesting
• Employee Stock Purchase Plan — buy Cars.com stock at a discount
• Unlimited Flex Time Off, 11 paid holidays, 1 volunteer day
• Paid parental and caregiver leave
• $350 one-time home office stipend + $70/month for virtual-first work
• Tuition reimbursement up to $5,250/year

•...and more — see our full Benefits, Perks & Culture here

Legal
For US-based positions: Applicants must be authorized to work in the United States. We're unable to sponsor employment visas at this time.

Cars.com is an equal opportunity employer and values diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

Applicants: click here to review our Privacy Policy for Applicants.
Current employees: click here to review our California Privacy Policy for Employees.