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Contractual Employment Specialist

Chicago Urban League
Chicago, IL Contractor
POSTED ON 10/19/2026
AVAILABLE BEFORE 2/9/2027

Department: Workforce Development
Employment Type: Contract
Compensation: $5,000 per month
Reports To: Director of Workforce Development


Position Summary

The Chicago Urban League is seeking a Contractual Employment Specialist to support the Workforce Development department in achieving job placement outcomes. The Contractor will work directly with young adults and adult participants to help them achieve their employment goals through individualized employment counseling and job placement.

This position works closely with Workforce Development staff and internal and external partners.

Key Responsibilities

  • Place a minimum of 35 program participants each month in full or part-time permanent positions, apprenticeships, occupational skills training, or post-secondary education opportunities.
  • Develop employment and internship opportunities for program participants.
  • Utilize your existing relationships with local employers, educational institutions, and training providers to achieve outcomes.
  • Assist participants with their job search, including the completion of job applications.
  • Work with young adult participants to complete Individual Employment Plans (IEPs).
  • Report placement information monthly, such as a hire letter, salary and wage information, and school or training enrollment.

Qualifications

  • Must have existing relationships with employers and have job placement experience.
  • Experience working with low-income populations.
  • Ability to work effectively under pressure in a fast-paced environment.
  • Experience assisting job seekers with resume development, interview preparation, job search strategies, and career planning.
  • Strong communication, interpersonal, networking, and relationship-building skills.
  • Proficiency with Microsoft Office, workforce management databases, applicant tracking systems, or similar data-tracking platforms.

Contract Compensation

This is a contractual position compensated at $5,000 per month.


To apply, send a cover letter and resume to careers@chiul.org and include “Contractual Employment Specialist” in the subject line.

Salary : $5,000

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