Assistant General Counsel, Transactions

Chicago Public Schools; United States; On-site; USD 87,000 - 116,000; Full time

Benefits offered by this job

Health insurance

Vision insurance

Behavioral health resources

Pension plan

FSAs

Job summary

Chicago Public Schools (CPS) seeks an Assistant General Counsel specializing in transactions to manage contracts and related legal matters. The role reports to the Deputy General Counsel and collaborates with colleagues within the Law Office and CPS departments.

The ideal candidate has experience in drafting commercial contracts, advising as a corporate generalist, and strong client counseling skills in a fast-paced setting.

Qualifications

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

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.

Skills

Analytical thinking

Client counseling

Time management

Independent work

Attention to detail

Deadline-driven

Problem solving

Communication

Judgment and integrity

Organization

Education

Bachelor’s degree

Juris Doctorate

Illinois bar admission

Tools

Google Suite

Microsoft Office

Contract management system software

Job description

Posting Date

Oct 9, 2026, 2:27:27 PM

Primary Location

Central-42 West Madison Street (Law Office)

CPS Non-Union Job Grade

S09

Estimated Annual Salary Range

87,000.00 - 115,500.00

Position Type

Non-Union Position

Overtime Status

Exempt

Final salary offers are dependent upon candidate qualifications.

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 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.

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.

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 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

Health & Wellness: Your Care, Your Choice

CPS 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 Options

• Pharmacy
• Vision
• Behavioral Health & EAP
• Employee Wellness Program

Financial Security: Planning for Today and Tomorrow

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

Work-Life Balance: Supporting Your Personal and Professional Life

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 temporary/part-time positions, however, all CPS employees must be residents of Illinois.

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