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Assistant General Counsel, Transactions Unit

Chicago Public Schools
Chicago, IL Full Time
POSTED ON 4/26/2025
AVAILABLE BEFORE 5/25/2025

Chicago Public Schools (CPS) is one of the largest school districts in the United States, serving over 340,000 students in 600 schools and employing nearly 36,000 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 Transactions Unit in the Law Office at Chicago Public Schools (CPS) drafts and negotiates a broad range of contracts including professional services, technology, equipment leases, educational services, and supply contracts. The Unit also provides legal review and counsel in bond issuances and other financings and advises departments and schools regarding compliance with Board rules, policies, and procurement laws.

Job Summary :

The Assistant General Counsel, Transactions will handle contracts and related legal issues, and address questions of substantial complexity in a deadline-driven, high-volume environment. The Assistant General Counsel will report to the Deputy General Counsel and will collaborate with staff across the Law Office and 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 :

  • Juris Doctorate from an accredited law school, required.
  • Licensed and authorized to practice law in the state of Illinois.
  • Experience Required :

  • Minimum of one (1) year legal experience, inclusive of internships, externships and / or clerkships
  • Experience working in Education, at a public agency, at a law firm and / or as in-house counsel is 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 steps
  • Highly skilled in commercial contract drafting and negotiations, and advising as a corporate generalist
  • Knowledgeable on a broad range of general legal matters, public procurement laws and risks impacting organizations
  • Strong client counseling background; 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
  • 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 :

  • 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.
  • Be Fully Vaccinated Against COVID-19 - Unless approved for a medical or religious exemption, all employees are required to be up-to-date on COVID-19 vaccinations, including boosters, and to submit proof of vaccination to the district within 30 days of hire. "Up-to-date" on vaccination is defined as being at least two weeks past all primary vaccine doses and any applicable boosters.
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