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Chicago Public Schools (CPS) is one of the largest school districts in the United States, serving over 320,000 students in 600+ schools and employing approximately 40,000 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.

The Juvenile Justice (JJ) Team is part of the Office of Student Support Engagement, which aims to overcome barriers to school engagement, particularly with the district’s highest-need and most disadvantaged students. The program offered by the Juvenile Justice Team is intended to ensure the successful transition of court-involved students to CPS district and options schools.  The goal is for arrested and detained students to return to school via a process where they feel safe, welcomed, engaged, and supported, and for schools to feel ready, prepared, and capable of integrating them back into the school community.

Job Summary: 

The Student Engagement Specialist will be responsible for reviewing and synthesizing CPS data, school input, student interviews/discussion, and family/P.O. collaboration to develop and implement school placements and transition plans for court-involved students, including those at the Cook County Juvenile Temporary Detention Center (JTDC).  This position will engage with students at court and in detention to interview them about their school histories, goals, interests, strengths, barriers, and concerns to determine a plan to re-engage the student in school.  They will communicate with principals, counselors, and deans to facilitate re-entry conferences at CPS schools, addressing obstacles to transition and promoting student voice, repairing broken relationships, and ensuring student needs are met. The Student Engagement Specialist will work with Probation, schools, and community partners to connect students to needed resources, including establishing linkages to resources in the neighborhood, and will monitor the student’s progress both while receiving services and after re-enrolling into school.  This individual will report to the Juvenile Justice Manager in the Office of Student Support and Engagement, which is part of the Office of College and Career Success. 

The Student Engagement Specialist will be held accountable for the following responsibilities:

• Develop a supportive and trusting relationship with high-need, court-involved students and identify the specific issues impacting student engagement in school and academic performance.

• Review student transcripts, records, and historical school data to guide student conversations, school placement recommendations, and transition/support plans.

• Collaborate with detention staff, CPS teachers and staff in student orientation, seminar classes, and individual transition planning.

• Communicate with students’ previous and proposed schools to gather input, make informed decisions, and plan for student re-entry.

• Utilize active listening, motivational interviewing, and empathetic, non-judgmental conversation to deeply engage with and learn about students.

• Work with students to establish academic and career interests and goals, and to utilize those in determination of best school fit.

• Work with school staff, Court/Probation staff, and community partners to develop transition plans to address social/emotional issues impacting performance.   

• Conduct re-entry meetings with students, parents, and school staff after student release from detention.

• Develop an understanding and knowledge of CPS school characteristics, key curricular and extracurricular offerings, and match students to best fit; ensure students are connected to support systems and personnel.

• Establish positive working relationships with school leadership and key staff members in order to advocate effectively with schools on behalf of students.

• Monitor student academic progress, attendance, and behavior; respond to changes in enrollment, attendance, and behavior.

• Conduct home visits and provide support to families in acquiring needed services to ensure student success.

• Assist students with exploring multiple educational pathways that meet their academic goals.

• Work with receiving schools to facilitate enrollment and monitor student persistence.

• Maintain a timely and accurate record of school recommendations, plans, and contacts in web-based CitySpan case management tool.

• Other duties as assigned. 

In order to be successful and achieve the above responsibilities, the Student Engagement Specialist must possess the following qualifications: 

Education Required: 

• High school diploma or GED equivalent is required

• Bachelor’s degree from an accredited college or university is highly preferred 

Experience Required: 

• Minimum of five (5) years of relevant professional experience in education, social services, health services, or related outreach work is required; 2 years of relevant professional experience may be considered in combination with a preferred degree.

• Experience working with court-involved students, high school students, and CPS schools, systems and policies preferred.

• Experience with Restorative Justice practices and Motivational Interviewing preferred.

• Language proficiency in both English and Spanish preferred

Knowledge, Skills, and Abilities: 

• Dedicated to providing every child with access to high quality education; acts as an advocate for students, and role models this behavior for fellow team members

• Committed to equity and access to educational opportunity for the most disadvantaged and marginalized students

• Comfortable working in a non-traditional learning environment; capable of working with minimal supervision outside of a formalized, central office setting

• Willingness to learn and adapt in the midst of new and shifting program and priorities with a "can-do," solutions-oriented approach to learning and problem solving

• Experience in creating and managing a student-friendly environment

• Strong interpersonal skills; demonstrated success building positive relationships with students, staff, and parents

• Outstanding organizational and time management skills; ability to maintain detailed files and records, prioritize workload and handle multiple competing priorities and deadlines

• Skilled in evaluating and meeting the social service needs of at-risk students, and coordinating the efforts of schools, Probation/Court services, and community organizations

• Strong written and verbal communication skills 

• Able to work flexible hours as needed to meet the needs of students and families

• Must possess computer skills including Microsoft Excel and Google Suite

Other requirements:

• Access to transportation to travel to other sites is required

• Valid Driver’s License and vehicle access preferred

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.

• Be Fully Vaccinated Against COVID-19 -Unless approved for a medical or religious exemption, all employees are required to be up-to-date on COVID-19 vaccinations, including boosters, and to submit proof of vaccination to the district within 30 days of hire. “Up-to-date” on vaccination is defined as being at least two weeks past all primary vaccine doses and any applicable boosters.