Director, Student Engagement

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 nearly 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.

Located within the Office of College and Career Success (OCCS), the mission of the Office of Student Support and Engagement (OSSE) is to partner with community-based organizations, schools and networks to establish and sustain supportive-learning communities founded on caring relationships and multi-tiered systems of support (MTSS) for students’ social, emotional, and behavioral needs.

The Student Engagement unit of OSSE promotes student connectedness and well-being, engagement in school, access, and participation in extracurricular activities geared toward providing students with experiences / resources before and after school hours.

This unit will support schools by providing funding and resources to offer students experiences, activities, and academic / social-emotional support that promotes connectedness and improves student outcomes.

Job Summary :

Reporting to the Executive Director of Student Support and Engagement, the Director of Student Engagement will lead a cross-functional team in identifying students at risk of disengagement (early warning indicators-student priority list) and supporting schools with establishing systems and structures of support to increase student connectedness and well-being, leading to a district-wide improvement in student outcomes (attendance, grade point average, graduation rates).

This position will support schools with the implementation of before and after-school programming and activities, equitably curating district-wide offerings of responsive extracurricular and mentoring programs, identifying gaps in offerings, and targeting student priority groups not served.

In addition to supporting school capacity-building and district accountability, the Director of Student Engagement will build connections across existing district structures and between CPS and relevant partner government agencies, research institutions, and community organizations.

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

• Provide strategic direction, leadership, and oversight of student engagement initiatives and programming
• Lead multi-disciplinary and cross-functional teams devoted to different aspects of student engagement (data, clinical support, academic interventions, system linkages, vendor management, process improvement, communications, professional development, school systems)
• Support managers with providing funding / resources for Out of School Time (OST), Academic Competitions and additional extra-curricular and enrichment programming
• Support student connectedness, belonging, engagement, and mentoring programs throughout the District
• Support and build systems and structures to provide equity of funding and monitor school expenditures
• Develop systems for program management, support, and evaluation
• Establish formal and informal partnerships with system stakeholders in city, county, and state government as well as the non-profit sector
• Manage a budget of up to fifty million dollars; manage and monitor grant applications, budgeting, and reporting for state, federal, and philanthropic funding opportunities
• Oversee the contracts and relationships with direct program providers in adherence with CPS procurement policies and expectations
• Develop case management and data systems for program management and evaluation
• Partner with CPS senior leadership and Network leadership to provide regular, actionable reporting of school and network metrics / data to monitor student engagement, funds expenditure, and address unique / specific school needs
• Engage with other school districts across the country around OST impact, research, and best practices
• Ensure collaboration across OCCS teams and other CPS departments to support implementation, program monitoring, best practices sharing, and cross-functional and collective impact
• Support additional workstreams and complete other duties as assigned or otherwise necessary for unit and departmental success

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

Education Required :

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

Experience Required :

• Minimum of seven (7) years of relevant professional work experience in school and / or district-level leadership, including the following, is required :
• Minimum of five (5) years of direct supervisory / management experience with responsibility for leading a team of direct reports
• Minimum of five (5) years of experience supporting students with diverse needs through school programs in a large organization
• Professional experience managing complex, large-scale projects involving high-level cross-school / cross-office collaboration
• Prior urban school district experience preferred

Other requirements :

• Access to transportation to travel between work sites is required
• Valid Driver’s License and vehicle access preferred

Knowledge, Skills and Abilities :

• Demonstrated expertise in teaching, coaching, and leading professional learning
• Knowledge of best practices in mentoring, student support, student engagement, youth programming, and developing engagement supports at multiple tiers
• Knowledge of best practices in academic interventions and supports at multiple tiers
• Expertise in guiding the analysis of data and data-based inquiry to ensure the identification of student risk factors and intervention needs
• Ability to collaborate and drive consensus on student needs and intervention plans across a diverse group of personnel
• Expertise in external community-based youth development / social services and referral processes
• Excellent multitasking and time management skills; ability to effectively achieve multiple goals and manage multiple projects simultaneously
• Strong team building and leadership skills; Capable of building and managing high-performing teams
• Entrepreneurial approach to re-thinking the landscape of extracurricular programming
• Deep commitment to equity and access

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.