Benefits Analyst — Remote-First with AI Tools

Cars.com LLC; Illinois; Hybrid; USD 65,000 - 79,000; Full time

Benefits offered by this job

Medical, Dental & Vision

Home office stipend

Generous PTO

Paid Holidays

Floating Holiday

Volunteer Day

Recharge Day

Job summary

Cars Commerce is a remote-first tech company in the automotive space seeking a Benefits Analyst to manage U.S. and Canada benefits and leaves within Total Rewards. You will ensure accurate enrollments, deductions, and compliance, while serving as the first point of contact for employees and HR partners.

You will lead open enrollment, coordinate with payroll and legal, and leverage AI tools to modernize workflows. This role reports to the Senior Manager, Benefits.

Qualifications

• Bachelor's degree in Human Resources, Business, or a related field; 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 requirements.
• Experience with Workday benefits configuration preferred.
• Proven ability to handle confidential information with discretion.

Responsibilities

• Administer self-funded medical, dental, vision, life, disability, FSA/HSA, commuter, COBRA and 401(k) programs for U.S. and Canadian employees.
• Lead annual open enrollment testing, support, and follow-up.
• Manage vendor invoicing, billing, and contract timelines.
• Pull benefits data and generate reports for leadership and Finance.
• Maintain intranet benefits content and communications calendar.

Skills

Analytical skills

Excel/Google Sheets

Communication skills

AI tools usage

Vendor coordination

Education

Bachelor's degree in Human Resources/Business

Tools

Workday (Benefits and Absence)

Google Workspace

Microsoft Office

HRIS

Job description

Cars Commerce is a remote-first tech company in the automotive space seeking a Benefits Analyst to manage U.S. and Canada benefits and leaves within Total Rewards. You will ensure accurate enrollments, deductions, and compliance, while serving as the first point of contact for employees and HR partners.

You will lead open enrollment, coordinate with payroll and legal, and leverage AI tools to modernize workflows. This role reports to the Senior Manager, Benefits.