Assistant General Counsel, Transactions

Posting Date

Feb 19, 2026, 8:33:11 PM

Central-42 West Madison Street (Law Office)

CPS Non-Union Job Grade : S09

87,000.

Position Type :
Non-Union Position

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.

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.

• Independently review, structure, draft, negotiate and advise on a wide range of contracts and transactions, including general services, technology, data sharing and protection, research, supply, financings, and related procurement documents and solicitations.
• Provide pragmatic, focused legal counsel to internal stakeholders on transactional matters, interpretation of contractual provisions, laws, CPS rules, and policies.
• Be an active, collaborative partner, applying combined operational and legal judgment to proposed deals, relationships and other issues requiring legal or compliance attention.
• Update and maintain accurate status and relevant information on assigned matters in unit databases.
• Other duties as assigned.

• Education Required:
  
  Bachelor’s degree from an accredited college or university.
• Education Required:
  
  Juris Doctorate from an accredited law school.
• Must be licensed to practice law and in good standing in the State of Illinois.
• Experience
  
  Required:
  
  Minimum of one (1) year of related legal experience, inclusive of internships, externships or clerkships. Experience working in Education, at a public agency, at a law firm, or as in-house counsel preferred.

• Excellent analytical skills; demonstrated ability to quickly grasp and effectively communicate complex concepts, define problems and analyze issues relating to contracts, statutes, policy and operations, and develop valid conclusions and action steps.
• Experience drafting a range of commercial contracts and advising as a corporate generalist.
• Strong client counseling background in a deadline-driven, high volume environment;
  Ability to provide sound legal advice in a short response time and work on multiple tasks simultaneously.
• Self-starter who takes initiative to advance and close out projects, is able to work independently and resolve matters efficiently.
• Demonstrated ability to take ownership of and solve problems, quickly assess issues, and provide sound legal advice to a wide variety of stakeholders, including senior leadership, school administrators and central office departments.
• Excellent communication and engagement skills (writing, client communications, speaking, listening).
• Exceptional judgment, integrity, honesty, credibility, and the courage to make difficult yet necessary decisions.
• Highly organized with excellent time management and organizational skills.
• Deadline-driven, strategic thinker.
• Detail-oriented and results-driven.
• Demonstrated success working in fast-paced, rapidly changing environment.
• Ability to use software systems, including a contract management system software.
• Proficiency with Google Suite (docs, sheets, slides) and Microsoft Office.

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

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

• CPS values the well-being of its employees and offers 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…