Benefits:

• Competitive salary
• Free uniforms
• Training & development

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

• Active Life and Health License for the State of Illinois (Illinois Department of Insurance).
• Willingness to work on-site at CPS schools and non-school facilities.
• Reliable transportation.
• Ability to pass the CPS background check.
• Strong communication and interpersonal skills to explain benefits to diverse groups.
• Comfort with technology (online enrollment platforms, laptops, mobile apps).

Preferred

• Prior experience in benefits counseling, enrollment support, or HR services.
• Flexible and adaptable to different work environments and schedules.
• Strong organizational skills and attention to compliance and detail.

Why Join Us?

• High daily pay with guaranteed base plus performance earnings.
• Impactful work supporting educators, staff, and community employees.
• Flexibility with opportunities for extra income through evenings and weekends.
• Career growth potential — exceptional candidates may transition into full-time or ongoing roles.