Deputy General Counsel

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Posting Date

May 29, 2025, 2 : 43 : 08 PM

Primary Location

Central-42 West Madison Street (Law Office)

CPS Non-Union Job Grade : S12

Position Type : Non-Union Position

Overtime Status

Exempt

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 Labor and Employee Discipline Unit in the Law Department at Chicago Public Schools (CPS) handles traditional labor law matters involving unfair labor practice charges and arbitration demands filed by labor organizations and unionized employee discipline administrative conferences and hearings for the district.

Job Summary :

The Deputy General Counsel will supervise, manage, and lead a team of attorneys and support staff, including an Assistant Deputy General Counsel, two Senior Assistant General Counsels, six Assistant General Counsels, a paralegal, and two legal secretaries. The Deputy General Counsel will report to the Managing Deputy General Counsel and the General Counsel. This is an exempt full‑time position that will be paid for time worked on a salary basis.

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

• Overseeing employee discipline and labor litigation, including principal and tenured teacher dismissal hearings, principal discipline conferences, school support staff dismissal hearings, grievance arbitrations, and unfair labor practice trials, including first‑ or second‑chairing hearings, arbitrations, and trials when appropriate;
• Supervising, managing, and leading attorneys, paraprofessionals, and support staff assigned to the Labor & Discipline Unit, including reviewing and editing written briefs, pleadings, and correspondence and advising on successful litigation strategy and case management techniques;
• Counseling chiefs, departments, and schools with respect to legal compliance requirements, significant labor and employee discipline matters, employment issues, settlements, and risk mitigation;
• Chairing the district’s Discipline Committee, including analyzing investigations and leading the discussion with a team of executive‑level employees to make disciplinary recommendations to district’s top executives;
• Oversee day‑to‑day operations, be a point of escalation from other offices across the district, and continuously work to develop and maintain morale within the Unit;
• Proactively manage risk and work to improve district efforts within labor and employee discipline;
• Assisting with the development and promulgation of Board policies;
• Manage outside counsel responsible for directly representing CPS in labor and employee discipline matters;
• Collaborate with Office of the Inspector General, Office of Student Protections, and the Law Department Investigations Unit with respect to matters under investigation by those offices;
• Presenting labor and employee discipline topics to school administrators and leaders at district’s annual legal conference and conducting training on same as needed to chiefs, school administrators, and Central Office teams;
• Other duties as assigned.

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

Education Required :

Must be licensed to practice law and in good standing in the state of Illinois

Experience Required :

Minimum of eight (8) years of legal practice responsible for litigation management, labor proceedings, and / or administrative law and proceedings, required

Minimum of five (5) years of leadership experience in a position involving the supervision / management and development of direct reporting attorneys and support staff of differing abilities, strongly preferred

Experience as a trial attorney with significant first chair experience, preferred

Knowledge, Skills and Abilities :

Experience managing and developing attorneys and support staff including team and morale building

Strong leadership skills, including in relationship building, employee motivation, conflict management, decision‑making, and delegation

Strong interpersonal skills and the ability to work collaboratively, and to communicate effectively, with multiple and diverse constituencies, including but not limited to : educators, staff, students, and union leaders

Strong negotiation skills, including the ability to persuade, plan, strategize and cooperate with operational goals in mind

Ability to build effective relationships throughout the Law Department, other Board departments, and with union partners

Ability to be a strategic thinker, analyze issues, formulate and evaluate alternatives, make sound, decisive recommendations, and accurately decide when to escalate

Exceptional advocacy, analytical, oral and written communication skills; Sound organizational skills with the ability to build efficient processes

Ability to manage numerous projects, cases, and subordinates simultaneously under pressure

Demonstrated ability to take ownership of and solve problems, to expeditiously assess issues and provide sound legal advice.

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.

Health & Wellness : Your Care, Your Choice

Financial Security : Planning for Today and Tomorrow

Work-Life Balance : Supporting Your Personal and Professional Life

We value the well‑being of our employees and offer competitive paid time off policies.

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