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Benefits:
- Competitive salary
- Training & development
NOW HIRINGÂ
BENEFITS COUNSELORS
Chicago Public Schools Open Enrollment 2026
Earn Up to $1,000 Per Day
Join United Schools Associates (USA), the official Benefits Enrollment Firm supporting Chicago Public Schools (CPS) during one of the largest public-sector Open Enrollment campaigns in Illinois.
Help more than 40,000 CPS employees understand their benefits and confidently complete their annual enrollment while earning outstanding compensation in a professional, team-oriented environment.
Assignment Type
Temporary Open Enrollment Project
October 22 – November 7, 2026
October 22 – November 7, 2026
WHY BENEFITS COUNSELORS CHOOSE USA
Competitive Compensation
- Earn up to $1,000 per day
- $300 Daily Guaranteed Compensation
- Elite Benefits Counselors: $400 Daily Guaranteed
- Performance Bonuses
- $200 Per Day Paid Training
WHY WORK WITH USA?
- Official Benefits Enrollment Firm for Chicago Public Schools
- Endorsed by the Chicago Teachers Union (CTU)
- A+ Better Business Bureau Rating
- More than 13 Years Serving Educators & Public Sector Employees
- Leadership Opportunities for Top Performers
WHAT YOU'LL DO
- Meet one-on-one and with groups of CPS employees to educate them about their employer-sponsored benefit options.
- Conduct benefits education sessions before school, during lunch periods, after school, and at scheduled employee meetings.
- Guide employees through the annual Open Enrollment process and assist them with completing their benefit elections accurately.
- Explain available benefit plans in a clear, professional, and unbiased manner so employees can make informed decisions.
- Answer employee questions while providing exceptional customer service and maintaining strict confidentiality.
- Promote employee engagement and encourage participation in the Open Enrollment campaign.
- Accurately document enrollment activity and follow all CPS, carrier, and USA enrollment procedures.
- Represent United Schools Associates professionally at assigned CPS schools and administrative worksites.
WHO WE'RE LOOKING FOR
- Current Illinois Life & Health Insurance License
- Strong communication and interpersonal skills
- Comfortable presenting to small groups and meeting one-on-one with employees
- Professional appearance and demeanor
- Reliable transportation
- Bilingual Spanish-speaking counselors are highly encouraged to apply
Previous enrollment or employee benefits experience is preferred but not required.
2026 OPEN ENROLLMENT SCHEDULE
Paid Training
October 22–24, 2026
Field Enrollment
October 26–November 7, 2026
No Sunday Assignments
No Sunday Assignments
Approximately:
- 2½ Paid Training Days
- 10 Field Enrollment Days
ABOUT UNITED SCHOOLS ASSOCIATES
United Schools Associates (USA) is a nationally recognized employee benefits education and enrollment firm specializing in serving school districts, municipalities, labor unions, and other public-sector organizations.
During the Chicago Public Schools Open Enrollment campaign, our Benefits Counselors help more than 40,000 CPS employees understand and enroll in their employer-sponsored benefits through personalized education, professional guidance, and exceptional customer service.
Our mission is simple:
Helping educators make informed benefits decisions with confidence.
USA PAYS FOR YOUR REQUIRED CPS BACKGROUND SCREENING
There is no cost to qualified candidates for the required CPS background screening. USA covers the cost as part of your onboarding.
Final Background Screening Deadline
Thursday, July 30, 2026
APPLY TODAY
Limited Positions Available
USA Talent Acquisition Team
Tanya Dy
Senior Recruitment Director
Senior Recruitment Director
Yolanda Williams
Recruitment Director
Recruitment Director
Fernando Bowie
Recruitment Director
Recruitment Director
☎ 844-USA-4YOU
844-872-4968
844-872-4968
jointheteam@usa4you.com
www.usa4you.com
WHY THIS OPPORTUNITY STANDS OUT
- Work on one of the largest public-sector benefits enrollment projects in Illinois.
- Build valuable Open Enrollment experience with a respected industry leader.
- Expand your professional network while serving Chicago educators and school employees.
- Be recognized and rewarded for outstanding performance.
Helping More Than 40,000 Chicago Public Schools Employees Make Confident Benefits Decisions.
United Schools Associates (USA)
Educating. Enrolling. Empowering.
Educating. Enrolling. Empowering.
Learn more about this Employer on their Career Site
