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, 2025

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 2025.