Benefits Counselors

United Schools Associates • Chicago, IL

16h • Onsite

About The Position

United Schools Associates (USA), the official benefits enrollment firm supporting Chicago Public Schools (CPS), is hiring Benefits Counselors for the 2026 CPS Open Enrollment campaign. Counselors will help more than 40,000 CPS employees understand employer-sponsored benefit options and complete annual enrollment. This is a temporary open-enrollment project running October 22 through November 7, 2026, with paid training October 22–24 and field enrollment October 26–November 7. The schedule includes approximately 2½ paid training days and 10 field enrollment days, with no Sunday assignments.

Counselors provide personalized benefits education and enrollment assistance at assigned CPS schools and administrative worksites. Compensation is $300–$1,000 per day, including a $300 daily guaranteed amount, up to $400 in daily performance bonuses for elite counselors, and $200 per day for paid training. USA covers the cost of the required CPS background screening for qualified candidates; the final screening deadline is July 30, 2026.

United Schools Associates is a nationally recognized employee benefits education and enrollment firm serving school districts, municipalities, labor unions, and other public-sector organizations. The organization describes itself as the official benefits enrollment firm for CPS, endorsed by the Chicago Teachers Union, with an A+ Better Business Bureau rating and more than 13 years serving educators and public-sector employees.

Requirements

• Current Illinois Life & Health Insurance License.
• Strong communication and interpersonal skills.
• Comfort presenting to small groups and meeting one-on-one with employees.
• Professional appearance and demeanor.
• Reliable transportation.

Nice To Haves

• Bilingual Spanish-speaking counselors are highly encouraged to apply.
• Previous enrollment or employee benefits experience is preferred but not required.

Responsibilities

• Meet one-on-one and with groups of CPS employees to explain employer-sponsored benefit options.
• Conduct benefits education sessions before school, during lunch periods, after school, and at scheduled employee meetings.
• Guide employees through annual Open Enrollment and help them complete benefit elections accurately.
• Explain available benefit plans clearly, professionally, and without bias so employees can make informed decisions.
• Answer employee questions, provide exceptional customer service, and maintain strict confidentiality.
• Promote employee engagement and encourage participation in the Open Enrollment campaign.
• Document enrollment activity accurately and follow CPS, carrier, and USA enrollment procedures.
• Represent United Schools Associates professionally at assigned CPS schools and administrative worksites.

Benefits

• Competitive salary.
• Training and development.
• Paid training at $200 per day.
• $300 daily guaranteed compensation.
• Performance bonuses of up to $400 per day for elite Benefits Counselors.
• USA covers the cost of the required CPS background screening for qualified candidates.
• Leadership opportunities for top performers.

What This Job Offers

• Education Level: No Education Listed