66 Degrees
Benefits Specialist
Chicago, IL +1 · Full-time · Posted Sep 29, 2026
- Location
- Chicago, IL
Chicago, Illinois, United States - Experience
- 2–4 years of direct experience in benefits administration, HR operations, or total rewards.
- Education
- Bachelor’s degree in Human Resources, Business Administration, or a related field, or equivalent practical experience.
- Visa sponsorship
- Cannot sponsor or transfer any visas, of any kind, at this time.
About the job
Administers employee benefits and leave programs, supports employees, handles enrollment and billing, and helps maintain benefits compliance.
What you'll do
- Manage benefits administration, enrollment changes, COBRA notifications, and employee benefits inquiries.
- Reconcile carrier invoices with payroll deductions and enrollment records; administer leave programs and support open enrollment.
- Support compliance reporting, audits, and benefits documentation, including Form 5500, ACA reporting, and Summary Plan Descriptions.
What they ask for
- 2–4 years of direct experience in benefits administration, HR operations, or total rewards.
- Hands-on experience transitioning a company from fully insured to self-funded.
- Solid knowledge of employee benefits regulations, including ERISA, ACA, COBRA, HIPAA, FMLA, and Section 125.
- Experience managing broker, TPA, and carrier relationships; advanced proficiency in Google Sheets.
Nice to have
- Rippling experience.
Tools
Rippling, Google Sheets, ERISA, ACA, FMLA, COBRA, HIPAA, Section 125
AI focus
No AI work in the role is stated; the posting says AI tools are used in recruitment, with final hiring decisions made by the human Talent Team.
Model-written summary · the original posting is authoritative