Assistant General Counsel, Labor & Employee Discipline

Posting Date Feb 19, 2026, 8:18:41 PM Primary Location Central-42 West Madison Street (Law Office) CPS Non-Union Job Grade : S09 Estimated Annual Salary Range 87,000.00 - 115,500.00 Position Type : Non-Union Position Overtime Status Exempt Final salary offers are dependent upon candidate qualifications. 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. Responsibilities Handle 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 handled 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 Qualifications Education Required Juris Doctorate from an ABA accredited law school Licensed to practice law and in good standing in the State of Illinois Experience Required Minimum of one (1) year post-JD legal experience, inclusive of internships, externships and/or clerkships, two (2) or more years, preferred Experience with negotiating and informally resolving complex cases Experience in labor, labor relations, employment, and/or administrative law strongly preferred Experience litigating cases in courts or in an administrative setting strongly preferred Experience drafting substantive motions and briefs strongly preferred Experience with oral and written client counseling and interviewing various types of witnesses strongly preferred Knowledge, Skills, and Abilities Ability to solve problems and work independently Effectively litigate cases 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 Oral and written communication skills Demonstrated ability to take ownership of and solve problems, assess issues, and provide sound legal advice Organizational skills and ability to manage many complex matters simultaneously 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 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 Competitive paid time off policies 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. 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