Deputy Chief of Schools, Options Schools

Chicago Public Schools; Chicago (IL); Hybrid; USD 120,000 - 180,000; Full time

Job summary

Chicago Public Schools seeks a Deputy Chief of Schools to support the Options School Network across 38 high schools. The role focuses on developing leaders, coaching principals, and ensuring high-quality instruction to improve graduation and postsecondary outcomes.

Required are a Bachelor's degree and an educator license, with a Master’s preferred. The position emphasizes strategic planning and cross‑functional collaboration within an urban district.

Qualifications

• Strong leadership and instructional expertise with a focus on school improvement.
• Ability to coach principals and develop leadership capacity.
• Experience in urban education settings preferred.

Responsibilities

• Support Options school leaders and operators to improve student outcomes.
• Develop and monitor strategic plans aligning with district goals.
• Provide actionable feedback to school leaders and drive school improvement.
• Coordinate leadership development plans and provide coaching support.
• Evaluate and report on school performance according to district expectations.

Skills

Executive leadership

Instructional leadership

Staff coaching

Strategic planning

Communication

Education

Bachelor's degree

Master’s degree preferred

Principal/Administrative license (PEL/ISA)

Job description

CPS Careers | Search | Apply | Get Hired

Primary Location

Central-4934 S Wabash Ave (Options Network)

CPS Non-Union Job Grade : S12

Position Type : Non-Union Position

Overtime Status

Exempt

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.

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:

Partner with the Chief of Schools to support Options school leaders and operators in the Network by:

Partnering with and developing their instructional leadership teams to develop, implement and monitor a strategic plan that helps meet student achievement goals. This includes assisting principals, operators, and their teams in engaging in root cause analyses, developing theories of action and building coherent multi‑year strategies.

Supporting principals’ and operators’ development and implementation of their school improvement plan, including the change management process needed to implement transformation initiatives at the school‑level.

Working with school leaders and operators to closely monitor school improvement through a cycle of continuous improvement and sound management practices.

For district run schools, providing frequent, actionable feedback to assist school leaders and operators and their leadership teams in improving in their leadership practice and achieving better results.

For district run Options Schools, in collaboration with the Chief of Schools, assess principal leadership capacity and develop, and support execution of individualized Leadership Development Plans (“LDPs”), which include providing weekly coaching support and conducting regular formal and informal evaluations to support the achievement of their performance scorecards and goals of the LDP

For contract, Alternative Learning Opportunity Programs, and charter schools, manage and/or support the evaluation and reporting of school performance against the District's academic, financial and operational expectations and the renewal of existing school contracts including application launch, evaluation, and community engagement to drive effective decision‑making.

As needed, manage the process for students transferring into Options Schools; ensuring Options Schools are following all transfer policies and procedures.

Co-design and deliver Network‑wide strategy for Options Team, principal and assistant principal PD planning and development focused on building and sustaining instructional leadership capacity.

Serve as liaison to Support Centers; monitor schools’ operational performance and compliance, resolve open issues, etc. and ensure principal and operator time can be focused on instructional leadership.

Collaborate with the Chief of Schools to develop a high‑performing community of principals and Options School leaders who leverage one another’s strengths and support one another in achieving shared goals. This may include network meetings, peer mentoring, and/or individual job‑embedded coaching focused on instructional leadership.

Work collaboratively with CPS, city, and non‑profit colleagues to support a rigorous and relevant high school learning experience for students who face significant barriers to high school graduation; implementing a strategic plan to dramatically increase student graduation rates and ensure students graduate with a personally meaningful post‑secondary plan.

As a representative of the Chief of Schools, demonstrate a high level of moral imperative to work in the best interest of children. Demonstration of high levels of instructional expertise, integrity, honesty, credibility, and courage to make difficult yet necessary decisions is a must.

Other duties as assigned

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

Education Required:

Bachelor's degree from accredited college or university

Master’s degree in Education preferred

Illinois State Board of Education Professional Educator License (PEL) or Educator License with Stipulations, with a Principal or General Administrative endorsement

Experience Required:

A minimum of three (3) years of experience teaching Pre K - 12; experience in an urban setting preferred

A minimum of four (4) complete school years of experience as a school principal or at least three (3) complete school years and at least one (1) year of experience in a district administration role; experience in an urban setting preferred

A minimum of three (3) years of experience coaching and mentoring educators preferred

Knowledge, Skills, and Abilities:

Possesses the ability to assist the Chief of Schools in articulating a vision, sets high standards, and effectively guides schools and principals to commit to high expectations for all students by setting actionable, measurable goals and seeing them through to completion.

Expertise in leadership development and instructional leadership. Able to coach principals to excellence, build capacity of instructional leadership teams, and develop meaningful and high impact professional development for school leaders.

Is a strong communicator; speaking, listening, and writing.

Project planning and strategic planning capabilities, including the ability to establish long‑term vision and goals, and the ability to align and manage activities toward execution of identified goals.

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

Is knowledgeable of instructional and leadership best practices, operations, management and organizational design and uses this knowledge to assist the Chief of Schools to ensure improved practice and student outcomes.

Builds collaborative relationships with a wide variety of constituent groups, including external partnerships, to ensure the entire system operates in the most effective manner possible to support school and principal needs.

Ability to define problems, analyze data, and outline valid conclusions and action steps.

Possess a track record of success as demonstrated by superior academic and professional achievement.

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

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:

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.

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