Senior Assistant General Counsel, Labor & Employee Discipline
Job Number: 2500032R
Posting Date: Oct 9, 2025, 10:12:50 AM
Primary Location: Central-42 West Madison Street (Law Office)
CPS Non-Union Job Grade: S10
Estimated Annual Salary Range : 100,000.00 - 133,000.00
Position Type: Non-Union Position
Overtime Status: Exempt
Final salary offers are dependent upon candidate qualifications.
JOB DESCRIPTION -
Chicago Public Schools (CPS) is a district on the rise, serving over 320,000 students in 500+ schools and employing over 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. The Labor and Employee Discipline Unit (“L&ED”) handles traditional labor law matters and appeals involving unfair labor practice charges and arbitration demands filed by labor organizations. Additionally, the Unit prosecutes employee discipline matters before administrative agencies and the Illinois State Board of Education.
Job Summary:
Reporting directly to the Deputy General Counsel, the L&ED Senior Assistant General Counsel will handle traditional labor law matters involving unfair labor practice charges and grievance arbitrations filed by labor organizations. Additionally, the Senior Assistant General Counsel will lead in the prosecuting of employee discipline matters before administrative agencies and the Illinois State Board of Education.
The Senior Assistant General Counsel will be accountable for the following responsibilities:
Defend the Board in labor arbitrations against various labor unions
Defend the Board in unfair labor practice proceedings before the Illinois Educational Labor Relations Board
Represent the Board in prosecuting termination proceedings before the Illinois State Board of Education and the CPS Office of Administrative Hearings
First-chair high-profile arbitrations, disciplinary proceedings, and termination hearings
Provide direction and strategy on labor and employee discipline matters for various internal stakeholders
Work closely with CPS senior-leadership 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
Assist in managing a team of six Assistant General Counsels and two legal support staff
On a daily basis, advise various CPS clients, including senior leadership, Network Chiefs, and school principals on labor and employee relations matters
Required Education:
Bachelor’s degree from an accredited college or university.
Juris Doctorate from an ABA-accredited law school.
Licensed and authorized to practice law in the state of Illinois.
Required Experience:
Minimum of five (5) years of legal practice in the labor and employment law area is required.
Additionally, experience in one of more of the following areas is strongly preferred: administrative law, labor relations, or state and/or federal court litigation.
Experience with management and leadership is preferred.
Knowledge, Skills, and Abilities:
Strong communication skills: speaking, listening, and writing
Ability to be a problem solver and independent worker
Effectively litigate cases before arbitrators, hearing officers, administrative agencies, and courts
Skills and abilities in management and leadership
Knowledge of best practices in employment and labor law, and federal and state-related law areas
Ability to build trusting relationships with, effectively advise, and work cohesively with Officers, Senior Leaders, Department Managers, and school-based staff on a variety of high-profile issues and cases
Highly organized with excellent time management and organizational skills
Proficiency with Google Suite (docs, sheets, slides) and Microsoft Office
Conditions of Employment
As a condition of employment with the Chicago Public Schools (CPS), employees are required to:
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
We understand the importance of financial stability, which is why CPS offers strong retirement and savings options:
- 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
CPS values the well-being of its employees and offers competitive paid time off policies:
- 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.