Senior Legal Assistant

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.

Job Summary:

Reporting to the Federal Litigation Unit’s Assistant Deputy General Counsel, the Senior Legal Assistant performs routine administrative duties for assigned attorneys and provides general administrative support across the Law Office, including complex legal support tasks. The Senior Legal Assistant also provides support and guidance to junior support staff. This role is of a confidential nature and has regular access to Law Office and other CPS Departments’ confidential files, data, and information, including confidential student and employee information.

This is a full‑time, non‑exempt position that will be paid for time worked on an hourly basis.

• Maintaining and tracking the unit’s docket of cases, including calendaring court dates, deadlines, and depositions.
• Maintaining and organizing the unit’s electronic case files.
• Ensures District compliance with settlement agreements.
• Opens and closes cases and matters in the Department’s Matter Management System following Unit and legal protocols in case maintenance.
• Obtains documents, payroll records, and other information to respond to subpoena and other requests.
• Reviews and edits work‑related tasks and responsibilities of administrative and legal assistants.
• Reviews investigatory and other reports to redact certain confidential information.
• Preparing drafts of appearances, subpoenas, deposition notices.
• Coordinating various aspects of case management and document delivery with outside counsel.
• E‑Filing in federal and state courts.
• Assists attorneys during depositions, hearings, arbitrations, mediations, settlement conferences, and trials, including preparing witness folders, scheduling, exhibits, subpoenas, and providing technology assistance.
• Inputs data and maintains databases (e.g., open and closed files); analyzes data and trends in the Unit; compiles and generates reports.
• Maintains cross‑Unit and/or cross‑Department databases and systems to support attorneys and ensure District compliance.
• Drafts and mails tailored compliance letters to employees and victims under Title IX requirements.
• Other duties as assigned.

• Associate degree from an accredited college or university and a minimum of five (5) years of administrative support or clerical work experience; or
• Bachelor’s degree from an accredited college or university and a minimum of three (3) years of administrative support or clerical work experience.

• Exceptional attention to detail with the ability to maintain accuracy while balancing multiple time‑sensitive priorities.
• Ability to review and interpret Unit and Department data and trends.
• Excellent organizational skills; demonstrated ability to organize and prioritize work in a dynamic, complex, fast‑paced environment to meet and manage competing deadlines.
• Able to take ownership of, and independently manage, tasks, timelines and systems, following tasks through to completion with little or no follow‑up; knows when to ask questions.
• Clear, effective verbal and non‑verbal communication skills (speaking, writing, listening).
• Ability to define problems, analyze data, and outline valid conclusions and action steps.
• Strong interpersonal skills and the ability to interact positively and professionally at all times with team members, other Law Department staff, executive offices, internal clients and external partners.
• Strong typing skills and proficiency using Microsoft Word, Excel, Google…