Job Title: Enrollment Benefits Specialist Group Voluntary Benefits

Job Description

Job DescriptionBenefits:

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

Company: United Schools Associates (USA)
Location: Chicago, IL (field-basedlocal 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 requiredpaid 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 relationsthis is your opportunity. With elite-level training, generous compensation, and a meaningful mission, USAs enrollment initiative with CPS is the place to be in 2025.