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Chicago Public Schools

Deputy Chief of Schools, Options Schools

4934 S Wabash Ave, Chicago, IL

On-site

First seen by offpeak October 22, 2026

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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.
 

Job Summary   

District-run CPS schools are organized into 18 networks and are provided administrative support, strategic direction, and leadership development by the Office of Network Support (ONS). By eliminating a one-size-fits-all network support model, schools benefit by having support that focuses exclusively on their needs. CPS principals, school leaders, and operators have access to their Network Chief as a resource and a liaison between their schools and district administration.

ONS is looking for a Deputy Chief of Schools to assist the Options School Network Chief for the Options School Network, a network of 38 high schools serving students all over the city. The Options Network consists of schools with multiple governing models (district run, contract, charter, and Alternative Learning Opportunity Programs); therefore the Deputy Chief must be adept at partnering directly with Charter management organizations and alternative education operators to improve outcomes for Chicago’s students. This position reports to the Chief of Options Network. With Options Schools playing a critical role in accomplishing the district’s vision, the Deputy Chief’s most important role is assisting the Chief of Options in supporting, developing and coaching school leaders and operators to ensure rigorous instruction and relevant, high impact student support that improves graduation rates and postsecondary outcomes for CPS’ Options school students.

The Deputy Chief of Schools will support the Chief in collaborating with and overseeing Options school leaders and principals to ensure that there is high quality instruction in every classroom and that the Options portfolio of schools is meeting the unique needs and aspirations of its targeted student population, ultimately increasing the graduation rates of students who face significant barriers to high school graduation. This is a full-time, exempt position that will be paid for time worked on a salary basis. 

The Deputy Chief of Schools will be held accountable for the following responsibilities:

 

In order to be successful and achieve the above responsibilities, the Chief of Schools must possess the following qualifications: 

Education Required: 

 

Experience Required: 

 

Knowledge, Skills, and Abilities: 

Benefits:

Health & Wellness: Your Care, Your Choice

CPS 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 the Chicago Public Schools: A Comprehensive Benefits Overview or the benefits handbook for comprehensive details.


Conditions of Employment

As a condition of employment with the Chicago Public Schools (CPS), employees are required to:

 

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