Senior Counsel, Complex Transactions

Chicago Public Schools; Chicago (IL); On-site; USD 85,000 - 115,000; Full time

Job summary

Chicago Public Schools (CPS) seeks a Senior Assistant General Counsel to manage complex contracts, procurement compliance, and transactional risk for a large urban district. You will draft, negotiate, and advise on a wide range of agreements, mentor junior attorneys, and partner with internal clients to align business and legal objectives.

You will lead contract templates, playbooks, and training, ensuring adherence to Board policies and state procurement laws while delivering timely advice in a

Qualifications

• 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 with high-volume workload.

Responsibilities

• Independently review, structure, draft, negotiate and advise on contracts and transactions with limited supervision.
• Provide mentoring and leadership to junior attorneys, paralegals and staff.
• Oversee negotiations, drafting and review to meet deadlines and policy requirements.
• Advise internal clients on business and legal risks and procurement compliance.
• Lead internal client meetings and guide on risks to teams.
• Develop and improve contracting protocols, templates, training, and playbooks.
• Research changes in laws and policies affecting transactions.

Skills

Contract drafting

Negotiation

Leadership

Project coordination

Client counseling

Time management

Communication

Analytical skills

Education

Juris Doctorate

Bachelor’s degree

Job description

Chicago Public Schools (CPS) seeks a Senior Assistant General Counsel to manage complex contracts, procurement compliance, and transactional risk for a large urban district. You will draft, negotiate, and advise on a wide range of agreements, mentor junior attorneys, and partner with internal clients to align business and legal objectives.

You will lead contract templates, playbooks, and training, ensuring adherence to Board policies and state procurement laws while delivering timely advice in a