Benefits Analyst

Cars.com LLC is hiring a Benefits Analyst to administer its U.S. and Canadian benefits and leave programs within Total Rewards. The role maintains accurate and compliant benefits operations, supports employees and internal partners, manages vendors and reporting, and oversees benefits communications.

Responsibilities

• 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
• 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
• 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
• 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
• 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

Skills

• 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
• 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
• Applicants must be authorized to work in the United States
• We are unable to sponsor employment visas at this time
• Benefits configuration experience in Workday
• 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

Benefits

• Some roles are eligible for bonus and/or equity programs, depending on level and role.
• Medical, Dental & Vision Healthcare Plans
• New Hire Stipend for Home Office Set-Up
• Generous PTO
• Paid Holidays, Floating Holiday, Volunteer Day, Recharge Day

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