Assistant General Counsel, Transactions
260002IS
: Oct 9, 2026, 2:27:27 PM
: Central-42 West Madison Street (Law Office)
CPS Non-Union Job Grade: S09
: 87,000.00 - 115,500.00
Position Type: Non-Union Position
: Exempt
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: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. In order to be successful and achieve the above responsibilities, the Assistant General Counsel must possess the following qualifications:
Education Required:Bachelor’s degree from an accredited college or university. 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.
Knowledge, Skills, and Abilities: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 stepsExperience drafting a range of commercial contracts and advising as a corporate generalistStrong 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 simultaneouslySelf-starter who takes initiative to advance and close out projects, is able to work independently and resolve matters efficientlyDemonstrated 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 decisionsHighly organized with excellent time management and organizational skills Deadline-driven, strategic thinkerDetail-oriented and results-drivenDemonstrated success working in fast-paced, rapidly changing environment Ability to use software systems, including a contract management system softwareProficiency with Google Suite (docs, sheets, slides) and Microsoft Office Benefits:Health & Wellness: Your Care, Your ChoiceCPS 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 OptionsPharmacyDentalVisionBehavioral Health & EAPEmployee Wellness ProgramFinancial Security: Planning for Today and TomorrowWe understand the importance of financial stability, which is why CPS offers strong retirement and savings options:Basic Life InsuranceLife and Disability InsurancePension PlansSupplemental Retirement Plans (403(b) and 457(b))Flexible Spending Accounts (FSAs)Spot Pet InsuranceWork-Life Balance: Supporting Your Personal and Professional LifeCPS values the well-being of its employees and offers competitive paid time off policies:Paid LeaveSick LeaveVacation DaysParental LeavesShort-Term DisabilityReligious HolidaysLeaves
Reference the Chicago Public Schools: A Comprehensive Benefits Overview or the benefits handbook for comprehensive details.
Conditions of EmploymentAs 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.
Chicago Public Schools is looking for teachers, leaders, and non-instructional staff to transform the face of urban education. We are a team of passionate, committed, and talented professionals who believe that every CPS student will graduate prepared for success in college, career, and life. Come join us in making CPS a model for public school districts throughout the nation. CPS is the third largest school district in the United States with more than 600 schools providing education to over 340,000 children.
