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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 Office departments, Networks, and schools on NBJ transition processes and requirements.

• Utilize CPS systems (Aspen, Dashboard, CitySpan) to analyze student academic history, create tailored school and intensive support recommendations, and facilitate student enrollment in accordance with CPS policy.

• Oversee improvements to the CitySpan case management system and perform regular quality assurance analyses of entered data to ensure accuracy in student tracking and reporting.

• Drive continuous program improvement by researching literature on juvenile justice re-entry, adopting evidence-based best practices, and implementing strategic initiatives to enhance student outcomes.

• Other duties as assigned 

In order to be successful and achieve the above responsibilities, the Juvenile Justice Re-Entry Team Lead must possess the following qualifications: 

Education Required: 

• Bachelor’s degree from an accredited college or university

Experience Required: 

• Minimum of five (5) years of professional experience in educational settings is required

  • Experience providing professional coaching to adults

  • Experience collaborating with stakeholders from multiple organizations and systems

  • Program and project management experience

• Experience with Chicago neighborhoods, schools, juvenile justice, and social services landscape, and a deep knowledge of and connection to resources within underserved and disinvested areas of Chicago is highly preferred

• Experience in a supervisory or management position leading a team of direct reports is preferred

• Bilingual - Spanish preferred

Other requirements:

• Access to transportation to travel to other sites is required

• Valid Driver’s License and vehicle access preferred

Knowledge, Skills, and Abilities:

• Ability to articulate a vision, set high standards, and effectively guide stakeholders in the realization of expectations set

• Effective strategic planning capabilities, including the ability to establish long-term vision and goals, and align/manage activities toward goal fulfillment

• Strong communication skills (speaking - including presentations - listening, and writing) and ability to  demonstrate and model effective communication and practices with adults, students, and families

• Understanding of adult behavior change and ability to respond effectively to resistance, skepticism, and diverging interests

• Training in restorative justice practices and motivational interviewing is preferred

• Understanding of the procedural and substantive challenges students face in returning from Juvenile Detention

• Skilled in conflict resolution and consensus-building among multiple stakeholders with diverse backgrounds, interests, and perspectives

• Belief in the ability of all students to succeed, and the ability of systems to change and adapt to their needs 

• Ability to define problems, analyze data, and outline valid conclusions and action steps; capable of using stakeholder input, outcomes, and data to manage processes, guide work, and evaluate success

• Strong leadership and team building skills, e.g., ability to develop high performing teams united around a clear vision for serving schools and achieving JJ student success

• Ability to build collaborative relationships with a variety of constituent groups, including external partners, to ensure the re-entry process operates in the most effective manner possible to support schools, JJ students, and families

Benefits:

Health Wellness:Your Care, Your ChoiceCPS is committed to providing comprehensive health coverage to our employees and their eligible dependents. You'll have access to a variety of choices to best fit your needs:

Medical Plan Options

Pharmacy

Dental

Vision

Behavioral Health EAP

Employee Wellness Program

Financial Security: Planning for Today and Tomorrow

We understand the importance of financial stability, which is why CPS offers strong retirement and savings options:

Basic Life Insurance

Life and Disability Insurance

Pension Plans

Supplemental Retirement Plans (403(b) and 457(b))

Flexible Spending Accounts (FSAs)

Spot Pet Insurance

Work-Life Balance: Supporting Your Personal and Professional Life

CPS values the well-being of its employees and offers competitive paid time off policies:

Paid Leave

Sick Leave

Vacation Days

Parental Leaves

Short-Term Disability

Religious Holidays

Leaves
 

Reference theChicago Public Schools: A Comprehensive Benefits Overviewor thebenefits handbookfor comprehensive details.

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. The Chicago residency requirement does not apply to temporary/part-time positions; however, all CPS employees must be residents of Illinois.