Seasonal Benefits Enrollment Counselor

Job Description

Job Description

SEASONAL BENEFIT ENROLLMENT COUNSELOR (NOT FULL TIME)

Open Enrollment : October 27 – November 7, 2025

Training : 2 days of paid training, October 23–24, 2025

Pay : Earn up to $800 per day (per diem guaranteed $350–$400; additional income based on enrollments)

Location : Chicago Public Schools campuses and non-school sites

About the Role

Join our team in helping Chicago Public Schools employees make informed choices about their benefits. As a Seasonal Benefits Enrollment Counselor , you’ll serve as the primary on-site representative during Open Enrollment. This high-impact role combines professional expertise with community service — and offers excellent daily pay, flexibility, and the potential for ongoing work.

What You’ll Do

• Serve as the dedicated counselor for assigned campuses and non-school sites (e.g., mechanic shops, transportation hubs, etc.).
• Provide consistent on-site support during Open Enrollment.
• Conduct both group and individual benefit sessions, including presentations at employee events like “Benefits with Breakfast.”
• Guide staff through enrollment in Core and Ancillary / Voluntary Benefits with clarity and care.
• Take advantage of additional income opportunities through extended work hours, available evenings and weekends during the Open Enrollment period.
• Complete paid training (Oct 23–24) to ensure expert-level knowledge of CPS benefits.

What We’re Looking For

Required

Preferred

Why Join Us?