Enrollment Benefits Specialist – Group Voluntary Benefits

Benefits:
Allowances
401(k)
Bonus based on performance
Competitive salary
Training & development

Company: United Schools Associates (USA)
Location: Chicago, IL (field-based—local travel required)
Job Type: Full-time
Compensation: Highly competitive base with performance bonuses, paid training, car allowance, gas allowance, and more

About the Opportunity

United Schools Associates (USA), in collaboration with Chicago Public Schools (CPS), is preparing for one of the most dynamic enrollment campaigns in the country. We are seeking Enrollment Benefits Specialists to support over 47,000 CPS employees during their evergreen open enrollment for their voluntary benefits services.

This role offers exceptional compensation, world-class training, and the chance to positively impact school staff and educators across Chicago.
Core Responsibilities

Educate and Enroll CPS employees on guaranteed issue, payroll-deducted voluntary benefits (e.g., short-term and long-term income protection, life insurance, accident, critical illness, hospital indemnity, and more)
Conduct engaging one-on-one or group presentations (in-person or virtual)
Guide employees through the digital enrollment process
Identify and qualify potential clients across schools and departments
Maintain accurate activity tracking and reporting
Educating clients about product knowledge and use of benefits
Collaborate with upper management and support staff on enrollment execution

Qualifications

Experience in benefits enrollment, insurance, or sales strongly preferred
State Life & Health Insurance License preferred (not required—paid training and bonus after passing the exam available)
Must be confident, self-motivated, and adaptable in a fast-paced environment
Strong presentation, communication, and interpersonal skills
Must be able to build rapport quickly and work both independently and in teams
Must be able to pass a background check to work in a school environment
Comfortable meeting deadlines and working under pressure
Ability to work flexible hours, including early mornings and once-a-week practice drill evening meeting
Must be based in or able to travel throughout Chicago for face-to-face school site visits
Must be fluent in English
Bilingual in Spanish is also preferred

Perks & Incentives

Car Allowance to support daily travel
Gas Allowance for commute and site visits
Production Bonus based on enrollment performance
Paid Training with expert industry mentors

Work Environment & Support

Field-based only – Specialists will visit CPS schools and offices directly
Extensive marketing resources, paid onboarding, and ongoing mentorship provided

Timeline

Onboarding begins: August 4, 2026

Why Join Us?

If you are a motivated professional looking to elevate your career in benefits, insurance, or client relations—this is your opportunity. With elite-level training, generous compensation, and a meaningful mission, USA’s enrollment initiative with CPS is the place to be in 2026.