Green Card Assistant General Counsel Jobs

Deputy General Counsel, Transactions

Job Number: 260002N3

Posting Date: Oct 29, 2026, 2:04:22 PM

Primary Location: Central-42 West Madison Street (Law Office)
CPS Non-Union Job Grade: S12
Position Type: Non-Union Position

Overtime Status: Exempt

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.

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 Deputy General Counsel will provide leadership, development and strategic direction to the Transactions Unit as they manage complex legal issues, execution of contracts and day to day operations. The Deputy General Counsel will report to the General Counsel, receive direction from the First Deputy General Counsel, and manage a team of direct reports. This is a full-time, exempt position that will be paid for time worked on a salary basis.

The Deputy General Counsel will be held accountable for the following responsibilities:

• Manage a team of attorneys, paralegals, and support personnel responsible for negotiating and drafting all of CPS’ contracts;
• Develop attorneys and staff to be solution orientated, client-focused and able to serve the operations of the District;
• Ensure compliance with all applicable laws, Board Rules, and Board Policies;
• Work closely with the Procurement Department and other CPS departments to prepare and review solicitations (e.g., Bids, Requests for Proposal, and Requests for Qualification, etc.);
• Develop efficient processes for tracking, preparing, negotiating, drafting, reviewing, approving, and executing contracts;
• Work towards the continuous improvement of the Law Department and actively participate in strategic planning and execution of Department goals;
• Manage outside counsel responsible for directly representing CPS in transaction matters and those firms working on CPS’ municipal finance transactions;
• Take a lead role on CPS’ most complex and critical agreements by counseling, negotiating, and drafting solicitations and contracts; and
• Perform additional duties as assigned.

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

Type of Education and License Required:

• Juris Doctorate degree 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

Type of Experience Required:

• Minimum of ten (10) years of relevant experience, including eight (8) years of legal practice and related transactional work, is required.
• Minimum of five (5) years of leadership experience in a position involving the supervision/management and development of direct reporting attorneys and support staff of differing abilities, strongly preferred.

Knowledge, Skills, and Abilities:

• Strong ability to develop working relationships, create processes and systems of improvement and efficiency, and engender the trust of internal and external clients;
• Exceptional advocacy, analytical, oral and written communication skills;
• Strong negotiation skills, including the ability to persuade, plan, strategize and cooperate with operational goals in mind;
• Ability to quickly analyze risk, prioritize concerns and accurately decide when to escalate;
• Ability to build effective relationships both internally throughout the Law Department, other Board departments, and with external vendors/partners;
• Sound organizational skills with the ability to build efficient processes;
• Ability to manage numerous projects simultaneously under pressure; and
• Demonstrated ability to take ownership of and solve problems, to expeditiously assess issues and provide sound legal advice.

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.