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Senior Assistant General Counsel, Transactions

Chicago Public Schools
Chicago, IL Full Time
POSTED ON 4/14/2025
AVAILABLE BEFORE 5/8/2025

Chicago Public Schools (CPS) is one of the largest school districts in the United States, serving over 320,000 students in 500 schools and employing approximately 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 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 Senior 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 through transactions. This Senior Assistant General Counsel will join the Transactions Unit and will report to the Deputy General Counsel. This is a full-time, exempt position that will be paid for time worked on a salary basis.

The Senior 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 with limited supervision, including general services, technology, data sharing, research, supply, financings, and related procurement documents and solicitations; ensure timely update of templates to reflect current legal and internal policy requirements.
  • Provide mentoring, leadership, direction, negotiation strategy support, and other skill-development advice to junior attorneys, paralegals, and staff.
  • Oversee contract negotiations, drafting and review of final work product, ensuring completion against established deadlines and compliance with Board rules, policies, and applicable laws.
  • Be an active business partner, applying combined business and legal judgment to proposed deals, relationships, and other issues requiring legal or compliance attention.
  • Lead internal client meetings, and provide guidance on business and legal risks to internal teams.
  • Advise and interpret laws and policies impacting transactions, contracting, and public procurement compliance.
  • Assist with the development and improvement of protocol and tools for contracting, including the development of contract templates, internal client training, implementation of systems to streamline contracting, and establishing playbooks, processes, and workflows.
  • Proactively research and report on changes in relevant laws, policies, and emerging trends.
  • Develop internal communications and training to ensure alignment in contracts and internal guidance documents.
  • Other duties and workstreams as assigned.

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

Education and License Required :

  • Juris Doctorate from an accredited law school, required
  • Must be licensed to practice law and in good standing in the State of Illinois
  • Experience Required :

  • Minimum of five (5) years of legal practice, required
  • Relevant commercial contracting experience, including relevant supervisory experience managing attorneys of differing abilities, strongly preferred
  • Experience working as in-house counsel within a public agency, preferred
  • Experience as a corporate generalist, including client counseling and management, ideally in a highly time-sensitive, deadline-driven, high-volume environment, preferred
  • Knowledge, Skills, and Abilities :

  • Expert-level experience in commercial contract drafting and negotiations, including technology and data agreements
  • Leadership and team-building skills
  • Communication and engagement skills (writing, speaking, listening, presentations)
  • Project coordination and time management skills with the ability to simultaneously manage a high volume of contract and advisory matters with limited supervision.
  • Ability to take ownership of and solve problems, to expeditiously assess issues, and provide sound legal advice to a wide variety of client types, including senior leadership, school administrators and staff, and Central office employees
  • Judgment, integrity, honesty, credibility, and the courage to make difficult yet necessary decisions.
  • Ability to provide legal advice in a short response time, work on multiple tasks simultaneously, and assist with supervision of the team
  • Analytical skills; able to quickly grasp and effectively communicate complex concepts
  • 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.
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