Deputy Chief, Law Office

Job Summary

Reporting to the General Counsel, the Deputy Chief, Law Office is a high-impact, senior leadership role responsible for driving the strategic execution, operational efficiency, and workplace culture of the Law Office in alignment with the General Counsel's vision and district-wide goals. Acting as a trusted advisor and primary liaison across internal and external stakeholders, this role oversees critical legal workstreams, including but not limited to FOIA, Policy, Ethics, and Records, while co-managing the Department’s multi-million dollar budget, performance metrics, and strategy by blending traditional performance management, mentorship, and continuing education outside counsel vendor relationships.

This leader oversees the Office’s business operations, policy initiatives, and specialized programs to foster a collaborative, high-performing environment. This is a full-time, exempt position that will be paid for time worked on a salary basis.

Responsibilities

• Provide direct oversight and leadership for multiple Law Office units, including but not limited to FOIA, Policy, Ethics, and Records, ensuring strict legal compliance and transparency
• Lead the development and implementation of departmental goals, ensuring alignment with the General Counsel’s vision and the district’s broader strategic priorities and ensuring all Office activities and initiatives comply with federal, state, and local laws, as well as Board rules and policies
• Evaluate and streamline administrative and legal workflows to increase efficiency and ensure the effective delivery of legal services to the Board
• Support continuous improvement initiatives in collaboration with District leadership
• Manage the full lifecycle of high-priority initiatives from initial planning to final execution (e.g., major projects and initiatives, after-action reviews, policy rollouts, etc.)
• Manage the development and implementation of departmental policies and procedures to ensure staff adhere to the highest standards of professional conduct
• Co-manage the Law Department’s annual budget, utilizing data and metrics to monitor performance, identify trends, and provide regular fiscal reports to the General Counsel
• Co-manage the Department’s ongoing reports to the Board and other reporting obligations, ensuring accuracy, conducting analysis, and trend-spotting
• Oversee Law Department vendor selection and management, including performance management for outside counsel and service providers to ensure high-quality support and cost-effectiveness and that spend is within Board authority
• Design, implement, and oversee departmental mentorship programs, peer groups, and continuing education paths; Align these growth initiatives with the annual performance review cycle to drive team capability and career progression
• Serve as the executive sponsor for the department’s Race & Equity Committee and Social Committee
• Actively cultivate an inclusive workplace culture through targeted programming, open forums, and community-building events; Manage internal departmental sub-committees and peer-to-peer support networks, ensuring team members have the resources, connection points, and advocacy needed to thrive
• Other duties and workstreams as assigned

Qualifications

• Education Required: Juris Doctor (JD) or Master’s Degree from accredited college or university required
• Experience Required: Minimum of ten (10) years of related professional experience, including the following is required: Minimum of seven (7) years in senior-level operations, legal administration, and/or strategic management within a high-volume environment (e.g., Director, Executive Director, Chief of Staff, Deputy General Counsel, etc.). Minimum of five (5) years experience supervising a team of direct reports
• Budget management experience
• Knowledge, Skills And Abilities: Expertise in public policy leadership and/or legal operations; Ability to maintain the highest standards of integrity; Ability to work collaboratively, and to communicate effectively, with multiple and diverse constituencies, such as staff, corporate partners, Board Members, and members of the district’s executive team; Strong and effective oral and written communication skills; Ability to analyze issues, formulate and evaluate alternatives, and make sound, decisive recommendations; Strong expertise in complex budget management and the optimization of resource allocation; Exceptional organizational and project management skills; Proven ability to lead teams through organizational transitions and drive the adoption of new systems or processes; Exceptional interpersonal skills with the ability to manage highly sensitive, confidential information; Poise to interact with, and instill confidence in, a wide variety of individuals, including Board members, executive staff, employees, local and federal government officials, outside counsel and the public

Conditions of Employment

• 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.