Juvenile Justice Re-Entry Team Lead

Posting Date

Posting Date:
Jan 29, 2026, 5:25:48 PM

Central-42 West Madison Street (CW Student Supprt and Engageme)

CPS Non-Union Job Grade : S07

Estimated Annual Salary Range: 66,000.

Position Type :
Non-Union Position

Exempt

Final salary offers are dependent upon candidate qualifications.

JOB DESCRIPTION ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

Chicago Public Schools (CPS) is a district on the rise, serving over 325,000 students in 500+ schools and employing over 45,000 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. Aligned with our transformed philosophy, we are steadfastly focused on ensuring that the District provides resources equitably to support every student, every school, and every community.

Six core values guide the work we do every day for our students – student-centered, whole child, equity, academic excellence, community partnership, and continuous learning. Each role in the district supports our vision that every student deserves a rigorous, joyful, and equitable learning experience.

The Office of Student Support & Engagement (OSSE) is tasked with bridging the persistent gaps that exist between schools and students, families, and communities. OSSE supports whole-school reform efforts to better engage families through the Community Schools Initiative, Out-of-School Time programming, and Attendance & Truancy procedures; and provides specific supports to engage historically marginalized and disenfranchised student populations: homeless students, youth in care, out-of-school and chronically absent students, and those with involvement in the juvenile justice system.

The Juvenile Justice team supports school engagement of court-involved CPS students.

Job Summary:

Reporting to the Juvenile Justice Manager, the Juvenile Justice Re-Entry Team Lead is responsible for developing, implementing, and overseeing the ongoing evaluation of the re-entry process for all CPS students at Nancy

B. Jefferson (NBJ). This position directly supervises Student Re-engagement Specialists and oversees student intake, assessment, transcript analysis, and caseload assignment. Additionally, the Team Lead manages the CPS Information Office and serves as the district’s representative at Cook County Juvenile Court. This role drives continuous improvement initiatives, leverages data-driven strategies, and fosters strong partnerships, acting as the primary liaison to school and Network leaders regarding NBJ transitions.

This is a full-time, exempt position that will be paid for time worked on a salary basis.

The Juvenile Justice Re-Entry Team Lead will be held accountable for the following responsibilities:

• Provide leadership, support, and evaluation for a team of Student Re-engagement Specialists, utilizing qualitative and quantitative data to review caseloads and ensure effective individual case management for 500-1000 NBJ students.
• Identify and collaborate with key district stakeholders (ODLSS, OSEL, ONS) to ensure holistic student support, while acting as the escalation point for resolving school and network-level conflicts.
• Serve as the primary District representative to Cook County Court partners (Judges, Probation, State's Attorneys), managing the daily exchange of confidential information and providing school records and consultation on CPS matters.
• Manage the daily intake, classification, and assignment of NBJ students based on geographic and risk criteria, while continuously refining the intake process to ensure efficiency and accuracy.
• Create systems to monitor Key Performance Indicators (KPIs) for re-entry success and establish a regular reporting mechanism to update CPS and Network leadership on outcomes.
• Develop and implement communication protocols and socialization plans to educate CPS Central…