Benefits Analyst - AI-Driven, Data-Savvy & Enrollment Expert

Cars.com; Chicago (IL); On-site; USD 65,000 - 79,000; Full time

Benefits offered by this job

Medical, Dental & Vision plans

Home Office stipend for new hires

Generous PTO

Paid holidays and floating holiday

Job summary

Cars Commerce is seeking a dedicated Benefits Analyst to manage U.S. and Canada benefits programs and leaves within Total Rewards.

You will handle enrollments, deductions, vendor billing, and leaves across Workday, serving as the primary contact for employees, HRBPs, Payroll, and vendors on benefits inquiries. This role suits someone who loves detail, process, and delivering clear answers during sensitive moments like births, medical events, and open enrollment.

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 leave requirements.
• Hands‑on experience with an HRIS, with benefits configuration in Workday strongly preferred.
• Strong analytical skills and advanced Excel or Google Sheets skills.
• Excellent attention to detail and the ability to meet recurring deadlines.
• Clear written and verbal communication with a service mindset and discretion with confidential information.
• Ability to work with multiple vendors, Payroll, HRBPs, and Legal simultaneously.
• Demonstrated curiosity and proficiency in using AI tools to boost productivity.

Responsibilities

• Administer self-funded medical, dental, vision, life, disability, FSA/HSA, commuter, COBRA, and 401(k) programs for U.S. and Canada employees.
• 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.
• Monitor eligibility rules, including ACA, and support compliance reporting.
• Support Canadian benefits administration alongside U.S. programs.
• Manage monthly LOA commission calculations in partnership with Payroll.
• Leverage AI tools to streamline workflows and drive efficiency.
• Champion adoption of emerging technologies to improve team output.

Skills

HR data analysis

Excel/Sheets

HRIS & Workday

Attention to detail

Communication skills

AI tools familiarity

Education

Bachelor's degree in HR/Business or related field

Equivalent experience

Tools

Workday

Google Workspace

Microsoft Office

Job description

Cars Commerce is seeking a dedicated Benefits Analyst to manage U.S. and Canada benefits programs and leaves within Total Rewards.

You will handle enrollments, deductions, vendor billing, and leaves across Workday, serving as the primary contact for employees, HRBPs, Payroll, and vendors on benefits inquiries. This role suits someone who loves detail, process, and delivering clear answers during sensitive moments like births, medical events, and open enrollment.