Top 198 Head of school Jobs in Illinois

Deputy Chief of Schools, High School Network
Chicago Public Schools —Chicago, IL
- $123,350 - $194,096 a year
- Full-time
- School experience
- High school
- Writing skills
- Wellness program
- Disability insurance
Chief of Schools - High School Network
Chicago Public Schools —Chicago, IL
- $141,853 - $223,209 a year
- Full-time
- School experience
- High school
- Office
- Wellness program
- Disability insurance
Chief Equity Officer
Chicago Public Schools —Chicago, IL
- $175,000 - $205,000 a year
- Full-time
- School experience
- 7 years
- Data analysis skills
- Wellness program
- Disability insurance
Chief People Officer
LEARN Charter School Network —Chicago, IL
- $210,000 - $225,000 a year
- Hybrid work
- Research
- Office
- 8 years
- Paid holidays
- Disability insurance
Quick Apply
Chief Schools Officer
Chicago Public Schools —Chicago, IL
- $200,000 - $235,000 a year
- School experience
- Office
- 3 years
- Wellness program
- Disability insurance
Head of Schools (Academy Grand/South)
UCAN —Chicago, IL
- $120,000 - $130,000 a year
- Weekends as needed
- 7 years
- Writing skills
- Master's degree
- Health savings account
- AD&D insurance
Quick Apply
Associate Head of School
Chicago Academy for the Arts —Chicago, IL
- From $70,000 a year
- Urgently hiring
- School experience
- High school
- Writing skills
- Health insurance
- Paid time off
Quick Apply
13d
Chief of Schools - Elementary School Network
Chicago Public Schools —Chicago, IL
- Full-time
- School experience
- Office
- Education
- Wellness program
- Disability insurance
Chicago Hope Academy High School - Cross Country Head Coach (Fall/Non-Teaching)
Chicago Hope Academy —Chicago, IL
- $1,250 a month
- Full-time
- Management
- High school
- Mid-level
Quick Apply
Pre-School Bus Driver - Head Start - Louisville, IL
CEFS Economic Opportunity Corp - Head Start Program —Flora, IL
- $17.53 an hour
- Full-time
- Background check
- CDL
- High school diploma or GED
- Health savings account
- Paid holidays
Quick Apply
Head Start School Bus Driver
C.E.F.S. Head Start 0-5 Program —Shelbyville, IL
- $17.53 an hour
- Full-time
- CDL
- High school diploma or GED
- Experience working with children
- Paid holidays
- Health insurance
Quick Apply
Head Start Lead Teacher for the 26/27 School Year (Start date August 2026)
Northwestern IL Community Action Agency —Freeport, IL
- $16.50 - $22.00 an hour
- Full-time
- School experience
- Classroom
- Spanish
- Health insurance
- Dental insurance
Quick Apply
11d
Chief Investigator
Chicago Public Schools —Chicago, IL
- $105,000 - $136,000 a year
- Full-time
- Office
- 3 years
- Analysis skills
- Wellness program
- Disability insurance
11d
Department Head Health, Physical Education, Science
Zion-Benton Township High School District 126 —Zion, IL
- $93,000 - $113,000 a year
- School experience
- High school
- Supervising experience
- Opportunities for advancement
Certified School Head Nurse
Champaign-Ford Regional Office of Education #9 —Champaign County, IL
- Classroom
- Nursing
- RN License
Head Of School
Excel Prep —Chicago, IL
- Full-time
- Classroom
- Education
- Doctor of Philosophy
- Health insurance
- Dental insurance
Quick Apply
Head Softball Coach (2026-2027 School Year)
Indian Prairie School District 204 —Aurora, IL
- High school
- Mid-level
- School
Head Lunch Supervisor
Schaumburg Community Consolidated School District 54 —Elk Grove Village, IL
- $27.50 an hour
- Part-time
- Management
- Mid-level
Head Custodian
Community Consolidated School District 15 —Palatine, IL
- $50,031 a year
- Full-time
- Senior level
- School
Deputy Chief, Law Office
Chicago Public Schools —Chicago, IL
- Full-time
- 5 years
- Office
- Master's degree
13d

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head of school jobs near illinois

Deputy Chief of Schools, High School Network

Chicago Public Schools -
Chicago, IL

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Job Details

Full-time
$123,350 - $194,096 a year

Benefits

Wellness program
457(b)
Disability insurance
Health insurance
Dental insurance
Flexible spending account
Paid time off
Pension plan
Employee assistance program
Vision insurance
403(b)
Life insurance
Pet insurance

Qualifications

School experience
Community partnership development
Professional development facilitation in schools
Organization design
Team leadership
Teacher training
Project planning
Writing skills
Strategic planning in education
Teacher mentoring for professional development
Leadership development
Team development
Instructional leadership in education
Teacher coaching
Data interpretation
Classroom experience
Leadership development programs
School staff supervision
Classroom Teaching
General management
Team building

Full Job Description

Deputy Chief of Schools, High School Network

Job Number: 260001HM

Posting Date: Jun 30, 2026, 3:20:41 PM

Primary Location: Central-42 West Madison Street (Network Support)

CPS Non-Union Job Grade: S12

Estimated Annual Salary Range : 123,350.00 - 194,096.00

Position Type: Non-Union Position

Overtime Status: Exempt

Final salary offers are dependent upon candidate qualifications.

JOB DESCRIPTION -

Chicago Public Schools (CPS) is the third-largest school district in the United States, serving over 340,000 students in 600+ schools and employing nearly 36,000 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.

Job Summary

The Deputy Chief of Schools will support the Chief of Schools in overseeing principals who are directly responsible for leveraging high-quality teaching in every classroom. 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:

Manage the transformation of schools and network support staff resulting in a dramatic increase in student achievement;
Partner with Chief of Schools to identify and recruit a strong pool of highly skilled principal candidates that are committed to a standard of excellence and can drive results;
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;
Manage Resource hub support in partnership with school leaders;
Design and deliver Network-wide principal and assistant principal professional learning focused on building and sustaining instructional leadership capacity;
Manage team administration and operations, including making sure that all team members are held accountable for meeting expectations;
Serve as liaison to Support Centers; monitor schools’ operational performance and compliance, resolve open issues, etc. and ensure principal time can be focused on instructional leadership;
Provide ad-hoc operational support to Principals and Network (escalated inquiries, emergencies, etc.);
Work collaboratively with fellow colleagues to support a seamless PreK-12 learning community, implementing a strategic plan to dramatically increase college and career readiness throughout the collaborative;
Apply knowledge of high school programming and goals to support members of the network support team and lead improved strategy at schools;
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; and
Performs additional ad hoc duties as assigned.

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

Education Required:

Master’s degree in Education or related field
Illinois State Board of Education Professional Educator License (PEL) or Educator License with Stipulations, with a Principal or General Administrative endorsement

Experience Required:

Minimum of three (3) years of experience teaching PreK-12; experience in an urban setting preferred
Minimum of four (4) complete school years of experience as a school principal or at least three (3) complete school years as a principal and one year (1) 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 the capacity of instructional leadership teams, and develop meaningful and high-impact professional development for school leaders.
Exceptional communications skills verbally, writing and listening.
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., the ability to develop high-performing teams united around a clear vision for serving schools and achieving student success.
Is knowledgeable of 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 the 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

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:

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.

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Refine Your Search

head of school jobs in illinois

Deputy Chief of Schools, High School Network

Chief of Schools - High School Network

Chief Equity Officer

Chief People Officer

Chief Schools Officer

Head of Schools (Academy Grand/South)

Associate Head of School

Chief of Schools - Elementary School Network

Chicago Hope Academy High School - Cross Country Head Coach (Fall/Non-Teaching)

Pre-School Bus Driver - Head Start - Louisville, IL

Head Start School Bus Driver

Head Start Lead Teacher for the 26/27 School Year (Start date August 2026)

Chief Investigator

Department Head Health, Physical Education, Science

Certified School Head Nurse

Head Of School

Head Softball Coach (2026-2027 School Year)

Head Lunch Supervisor

Head Custodian

Deputy Chief, Law Office

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