Assistant General Counsel, Labor Relations

Chicago Public Schools (CPS) is a district on the rise, serving over 325,000 students in 500 schools and employing over 45,000 people, most of them teachers. CPS has set ambitious goals to ensure that every student, in every school and every neighborhood, has access to a world-class learning experience that prepares each for success in college, career, and civic life. In order to fulfill this mission, we make three commitments to our students, their families, and all Chicagoans: academic progress, financial stability, and integrity. Six core values are embedded within these commitments – student-centered, whole child, equity, academic excellence, community partnership, and continuous learning.

With a workforce of 42,307 employees, the Labor Relations team collaborates closely with various labor unions to negotiate wages, hours, and other essential terms of employment. The collective bargaining rights of CPS employees are protected under the Illinois Educational Labor Relations Act (115 ILCS 5/1 et seq.) and the Illinois School Code (105 ILCS 5/34-1 et seq.). The Illinois Educational Labor Relations Board ensures compliance with these laws.

Job Summary

CPS is seeking an Assistant General Counsel who will work in the Labor Relations Unit of the Law Department. Reporting to the Chief Labor Relations Officer, the Assistant General Counsel will assist in administering and implementing collective bargaining agreements, conducting collective bargaining, advising principals and department leaders on matters related to collective bargaining agreements and labor relations, including discipline matters, drafting collective bargaining and grievance settlement agreements, and generally representing CPS in engagement with its labor partners. This is a full-time, exempt position that will be paid for time worked on a salary basis.

The Assistant General Counsel will be held accountable for the following responsibilities:

• Engaging with district principals and union representatives on labor issues, including advising CPS managers on best practices, contractual obligations, and creative problem solving.
• Meeting regularly with labor representatives to address contractual issues in order to avoid unnecessary grievances.
• Representing CPS in contract negotiations, other collective bargaining sessions, and impact bargaining discussions with labor unions representing CPS’ 30,000 plus unionized employees.
• Drafting responses to requests for information, grievance settlement agreements, and policy materials.
  
  

In order to be successful and achieve the above responsibilities, the Assistant General Counsel must possess the following qualifications:

Education Required

• Juris Doctorate from an accredited law school, required;
• Must be licensed to practice law and in good standing in the State of Illinois.
  
  

Experience Required

• A minimum of one (1) year of legal practice, inclusive of internships, externships and clerkships, required. Experience in labor and employment law, preferred.
  
  

Knowledge, Skills, And Abilities

• Communication and engagement skills (writing, client communications, speaking, listening)
• Interpersonal skills that will help build trusting internal and external stakeholder relationships
• Problem-solving skills, including a demonstrated ability to take ownership of and solve problems, quickly assess issues, and provide sound legal advice to a wide variety of stakeholders, including senior leadership, school administrators, and central office departments
• Experience advising clients on and representing clients in labor arbitration and mediation cases and other forms of alternative dispute resolution
• Knowledge of best practices in labor relations, federal and state labor and employment laws, administrative law, and related federal and state laws
• Strong client counseling skills in a deadline-driven, high-volume environment, including the ability to provide sound legal advice in a short response time and work on multiple tasks simultaneously
• Self-starter who takes initiative to advance and close projects and can work independently to resolve matters efficiently
• Highly organized with excellent time management and organizational skills
• Deadline-driven, strategic thinker
• Detail-oriented and results-driven
• Demonstrated success working in a fast-paced, rapidly changing environment
• Proficiency with Google Suite (docs, sheets, slides)
  
  

Conditions of Employment

As a condition of employment with the Chicago Public Schools (CPS), employees are required to:

• Establish/Maintain Chicago Residency - Employees are required to live within the geographic boundaries of the City of Chicago within six months of their CPS hire date and maintain residency throughout their employment with the district. The Chicago residency requirement does not apply to temporary/part-time positions, however, all CPS employees must be residents of Illinois.
  
  

Posting Date

Jul 22, 2026, 10:15:12 AM

Primary Location

Central-42 West Madison Street (Law Office)

CPS Non-Union Job Grade

S09

Estimated Annual Salary Range

87,000.00

Position Type

Non-Union Position

Overtime Status

Exempt