Benefits Analyst

Cars.com • Chicago, IL

17d

About The Position

The Benefits Analyst is the day-to-day administrator of Cars.com’s U.S. and Canadian benefits and leave programs within Total Rewards, reporting to the Senior Manager, Benefits. The role maintains accurate and compliant enrollments, deductions, vendor billing, and leave administration across Workday and benefit carriers. It also serves as a primary contact for employees, HR Business Partners, Payroll, and vendors on benefits and leave questions, handling sensitive personal and medical information with discretion.

The analyst administers benefit plans and leave programs, supports open enrollment, coordinates with vendors and internal partners, and prepares benefits reporting. The role also owns and updates intranet benefits and leave content and coordinates employee communications. It is suited to someone who is detail-oriented, process-focused, and able to provide clear answers to employees.

Requirements

• 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, state paid leave, and paid sick requirements.
• Ability to monitor, interpret, and maintain compliance with evolving federal, state, and local statutory leave laws and sick leave mandates.
• Hands-on HRIS experience; benefits configuration experience in Workday is strongly preferred.
• Strong analytical skills and advanced Excel or Google Sheets skills, including lookups, pivots, and data reconciliation.
• Excellent attention to detail and ability to manage recurring deadlines, including payroll cutoffs, invoice approvals, and enrollment windows.
• Clear written and verbal communication, service mindset, and sound judgment handling confidential information.
• Ability to work with multiple vendors, Payroll, HRBPs, and Legal at once.
• Curiosity and proficiency in using AI tools such as Gemini, Claude, Copilot, or role-specific AI platforms to improve personal and team productivity.
• Forward-thinking mindset and eagerness to explore, evaluate, and adopt AI capabilities to refine business processes.

Nice To Haves

• 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.

Responsibilities

• Administer U.S. and Canadian medical, dental, vision, life, disability, FSA/HSA, commuter, COBRA, and 401(k) programs, including enrollments, qualifying life events, terminations, and eligibility.
• Configure and maintain benefits in Workday and partner with HRIS on releases and testing.
• Lead annual open enrollment, including testing, employee support, and follow-up.
• Generate and process billing and invoices for self-funded health and state leave plans, ensuring compliance with plan parameters and vendor specifications.
• Monitor eligibility rules, including ACA benefit eligibility, and support ACA compliance reporting and temporary-employee guidelines.
• Support Canadian benefits administration, including carrier coordination and employee communications.
• Manage monthly LOA commission calculations with Payroll to ensure accurate payouts and policy compliance.
• Use AI tools and modern technologies to streamline workflows, automate repetitive tasks, and improve efficiency; champion adoption of emerging tools.
• Administer FMLA, parental, caregiver, medical, military, and state paid leave programs in partnership with the leave vendor.
• Partner with HR Business Partners, Payroll, and Legal on leave cases and employee questions.
• Serve as day-to-day contact for carriers, vendors, and the benefits consultant.
• Manage recurring vendor invoicing and funding approvals, reconcile billing discrepancies, and support annual renewals and vendor contract timelines.
• Pull and analyze benefits data, including employer contribution reports, enrollment counts, and leave metrics, for Total Rewards leadership and Finance.
• Support 401(k) administration, the annual audit, and the investment committee; maintain process documentation.
• Respond accurately and discreetly to employee, HRBP, and manager questions while protecting confidential information.
• Own and refresh benefits and leave content on the intranet.
• Build and maintain a benefits communications calendar for open enrollment, new-hire and life-event reminders, vendor programs, and policy changes.
• Partner with Internal Communications to draft, review, and schedule employee emails, FAQs, benefits guides, and webinars.
• Coordinate with vendors on co-branded or vendor-provided materials and verify that messaging reflects plan details and U.S./Canada differences.

Benefits

• Medical, dental, and vision healthcare plans.
• New-hire stipend for home office setup.
• Generous PTO.
• Paid holidays, floating holiday, volunteer day, and recharge day.
• Some roles may be eligible for bonus and/or equity programs, depending on level and role.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level