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Chicago Public Schools

Assistant General Counsel, Transactions

42 West Madison Street, Chicago, IL

On-site

First seen by offpeak October 22, 2026

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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.
 

CPS is seeking an experienced attorney who can hit the ground running in the Transactions Unit as Assistant General Counsel.  The successful candidate must have experience in commercial contract drafting and negotiations, demonstrated corporate generalist experience and strong client counseling background in a deadline-driven, high volume environment.  The Assistant General Counsel will handle contracts and related legal issues and questions of substantial complexity and must have a broad range of knowledge and skill on general legal matters, public procurement laws and risks impacting organizations.


Job Summary: 

CPS seeks an Assistant General Counsel specializing in transactions. This role will involve managing contracts and related legal matters, requiring the ability to address complex issues  in a deadline-driven, high-volume environment. The Assistant General Counsel will report to the Deputy General Counsel and will collaborate with colleagues within the Law Office and across various CPS departments.

 

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

 

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


Education Required:


Experience Required:



Knowledge, Skills, and Abilities:

 

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.


Conditions of Employment

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


 

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