Job Description

Job Description

Job Description

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. 

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