Senior Assistant General Counsel, Transactions

Chicago Public Schools (CPS) is a district on the rise, serving over 325,000 students in 500+ schools and employing over 45,000 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 Department at Chicago Public Schools (CPS) proactively mitigates risk and liability by carefully structuring and negotiating a broad range of contracts including professional services, technology, equipment leases, educational services, and supply contracts.

The Unit also provides ongoing legal counsel throughout the transactional process and advises departments and schools regarding compliance with Board rules, policies, and procurement laws.

Job Summary

Reporting to the Assistant Deputy General Counsel and Deputy General Counsel, 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 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, 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 development and improvement of protocol and tools for contracting, including development of contract templates, internal client training, implementation of systems to streamline contracting, 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 as assigned

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

Education Required

• Juris Doctorate from an accredited law school.
• Bachelor’s degree from an accredited college or university.
• Must be licensed to practice law and in good standing in the State of Illinois.

Experience Required

• Minimum of 5 years relevant commercial contracting experience, including a minimum of 2 years of successful and relevant supervisory experience managing attorneys of differing abilities.
• 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.
• Strong leadership and team building skills.
• Excellent communication and engagement skills (writing, speaking, listening, presentations)
• Excellent project coordination and time management skills with the ability to simultaneously manage a high volume of contract and advisory matters with limited supervision.
• Demonstrated 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.
• Exceptional 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.
• Excellent 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.

Posting Date

Jul 27, 2026, 3:00:58 PM

Primary Location

Central-42 West Madison Street (Law Office)

CPS Non-Union Job Grade

S10

Estimated Annual Salary Range

100,000.00

Position Type

Non-Union Position

Overtime Status

Exempt