Assistant General Counsel, Labor and Employee Discipline

Chicago Public Schools; Chicago (IL); On-site; USD 74,000 - 100,000; Full time

Benefits offered by this job

Health coverage

Pension plans

FSAs

Paid leave

Job summary

Chicago Public Schools is seeking an Assistant General Counsel, Labor and Employee Discipline to handle labor relations matters, arbitrations, and employee discipline appeals. This exempt, full-time role reports to the Deputy General Counsel and supports CPS clients, including school principals, with complex labor law issues.

The position requires a JD from an ABA-accredited school and active IL license, with at least one year of post-JD experience.

Qualifications

• Juris Doctorate from an ABA accredited law school is required.
• Licensed to practice law and in good standing in Illinois is required.

Responsibilities

• Litigate grievances, arbitrations, and discipline hearings.
• Advise CPS clients on labor and employee relations matters.
• Review legality of employee relations strategies using federal/state law knowledge.
• Defend CPS Board in labor arbitrations and administrative hearings.
• Represent Board before IEDRB and ISBE/Office of Administrative Hearings.
• Assist in advising CPS principals and internal clients on cases.

Skills

Litigation counsel

Client counseling

Oral & written communication

Organizational skills

Problem solving

Education

Juris Doctorate

Licensed to practice law in Illinois

Job description

Chicago Public Schools (CPS) is one of the largest school districts in the United States, serving over 320,000 students in 500+ schools and employing nearly 44,000 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.

The CPS Law Department provides a full array of legal services to the Chicago Board of Education and the various departments and divisions of Chicago Public Schools.

Job Summary

Reporting directly to the Deputy General Counsel and dotted line reporting to the Assistant Deputy General Counsel, Labor and Employee Discipline will work to handle traditional labor law matters and appeals involving unfair labor practice charges and arbitration demands filed by labor organizations. Additionally, the Assistant General Counsel will assist in the prosecuting of employee discipline matters before administrative agencies and the Illinois State Board of Education. This is a full-time, exempt position that will be paid for time worked on a salary basis.

The Assistant General Counsel, Labor and Employee Discipline will be held accountable for the following responsibilities:

• Work up and litigate grievance arbitrations, unfair labor practice charges, employee discipline administrative hearings, and other labor relations matters
• Work closely with CPS clients to ensure that labor and employee discipline cases are properly addressed and litigated
• Review the legality of employee relations strategies and policies utilizing a keen knowledge of federal and state statutory and case law in employment and labor areas, as well as all areas that may impact the District
• Defend the Board in labor arbitrations against various labor unions
• Defend the Board in unfair labor practice proceedings in front of the Illinois Educational Labor Relations Board, and represent the Board in termination proceedings in front of the Illinois State Board of Education and the CPS Office of Administrative Hearings
• On a daily basis, advise various internal CPS clients and school principals on labor and employee relations cases
• Other duties as assigned

Education Required

• Juris Doctorate from an ABA accredited law school is required
• Licensed to practice law and in good standing in the State of Illinois is required

Experience Required

• Minimum of one (1) year post-JD legal experience, inclusive of internships, externships and/or clerkships, including the following is required:
• Experience with negotiating and informally resolving complex cases
• Experience in labor, labor relations, employment, and/or administrative law strongly is preferred
• Experience litigating cases in courts or in an administrative setting is strongly preferred
• Experience drafting substantive motions and briefs is strongly preferred
• Experience with oral and written client counseling and interviewing various types of witnesses is strongly preferred

Knowledge, Skills, And Abilities

• Ability to litigate complex cases effectively before arbitrators, hearing officers, administrative agencies, and courts
• Knowledge of best practices in employment and labor law, administrative law, and federal and state-related law areas
• Ability to build trusting relationships and function effectively with officers, senior leaders, department managers, and school-based staff
• Ability to work in teams and independently, make effective decisions, and collaborate with clients
• Exceptional oral and written communication skills, including the ability to draft complex legal documents, deliver persuasive arguments, and translate intricate legal concepts for non-legal stakeholders
• Advanced organizational and case-management skills, with a proven ability to prioritize competing deadlines and oversee multiple complex legal matters simultaneously
• Demonstrated ability to take ownership of and solve problems, assess issues, and provide sound legal advice

Benefits

Health & Wellness: Your Care, Your Choice

CPS Is Committed To Providing Comprehensive Health Coverage To Our Employees And Their Eligible Dependents. You'll Have Access To a Variety Of Choices To Best Fit Your Needs

• Medical Plan Options
• Pharmacy
• Dental
• Vision
• Behavioral Health & EAP
• Employee Wellness Program

Financial Security: Planning for Today and Tomorrow

• Basic Life Insurance
• Life and Disability Insurance
• Pension Plans
• Supplemental Retirement Plans (403(b) and 457(b))
• Flexible Spending Accounts (FSAs)
• Spot Pet Insurance

Work-Life Balance: Supporting Your Personal and Professional Life

• Paid Leave
• Sick Leave
• Vacation Days
• Parental Leaves
• Short-Term Disability
• Religious Holidays
• Leaves

Reference the Chicago Public Schools: A Comprehensive Benefits Overview or the benefits handbook for comprehensive details.

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

Sep 2, 2026, 5:08:45 PM

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