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School Leadership Jobs in Chicago
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School Leadership
Guidepost Montessori
Region: Illinois Flexible Director Direct
School Leadership
Guidepost Montessori
Southern California Onsite Manager Direct
Assistant Principal - High School
KIPP Public Schools Northern California
San Francisco, CA, United States Onsite entry Direct
Head of School
Guidepost Global Education
Singapore Onsite Direct
Head of School (School Director)
Guidepost Montessori
Naperville, Illinois, United States Onsite Director Direct
KIPP - Science Teacher - Middle School (26-27)
KIPP
San Francisco, CA, United States Onsite mid Direct
Middle School: Dean of Instruction 2026-2027
TEXAS Onsite Direct
Chief of Schools
TEXAS-SUGAR LAND-ADMINISTRATION BUILDING ANNEX Onsite Executive Direct
Leadership Development Associate
Alphabe Insight Inc
Oklahoma City, OK, United States Onsite entry Direct
2026-27 Middle School Physical Education Teacher
KIPP Nashville Public Schools
Nashville, TN, United States Onsite mid Direct
Client Leadership Manager
WPP Media
Warszawa, Masovian Voivodeship, Poland Hybrid Manager Direct
[2026-2027] Licensed School-Based Mental Health Clinician (Lead)
Effective School Solutions
Lakeland, Florida, United States Onsite Lead Direct
School Counselor
River Rock Academy
Newville, PA Onsite Direct
High School Math Teacher
IOTA Community Schools
Memphis, TN, United States Onsite not-applicable Direct
School Counselor
Virtual Preparatory Academy of Ohio
Virtual Preparatory Academy of Ohio Remote Direct
Middle School Science Teacher
IOTA Community Schools
Memphis, TN, United States Onsite not-applicable Direct
Client Service Leadership
Global Elite Empire Consultants
Carson City, Nevada Remote Direct
Harvard Divinity School Librarian
Harvard University
Cambridge, MA, United States Onsite not-applicable Direct
Client Service Leadership
Global Elite Empire Consultants
Nashua, New Hampshire Remote Direct
Psychologist-Middle School (2026-2027 School Year)
Coleman Middle School
Coleman Middle School Onsite Direct
High School: Dean of Instruction 2026-2027
TEXAS Onsite Direct
High School Principal
TEXAS-SUGAR LAND-AUSTIN HIGH SCHOOL Onsite Direct
RBT School Based
BAYADA Home Health Care
Behavioral Health - Field Direct
Community School Coordinator
Colvin Elementary School
Colvin Elementary School Onsite Direct
Project Manager (School Construction)
Downey, CA Onsite Direct
Client Service Leadership
Global Elite Empire Consultants
Farmington, New Mexico Remote Direct
Client Service Leadership
Global Elite Empire Consultants
Simpsonville, South Carolina Remote Direct
Client Service Leadership
Global Elite Empire Consultants
Annadale, Virginia Remote Direct
School Counselor - 2026-2027 School Year
River Rock Academy
Johnstown, PA Onsite Direct
Client Service Leadership
Global Elite Empire Consultants
Lawton, Oklahoma Remote Direct
Virtual Middle School Teacher (2026 - 2027 School Year)
Trailhead Virtual Academy
Trailhead Virtual Academy Flexible Direct
Virtual School Counselor
Trailhead Virtual Academy
Trailhead Virtual Academy Remote Direct
High School: Professional School Counselor 2026-2027
TEXAS Onsite Direct
Director of HVAC School
UHP
Gentry (UHP Campus) Onsite Director Direct
Middle School Science Teacher (2026-27 School Year)
Prodeo Academy
Columbia Heights, MN Onsite Direct
1:1 School Nurse (RN)
BAYADA Home Health Care
Field Flexible Direct
Nurse-Elementary (2026-2027 School Year)
O K Elementary School Onsite Direct
Leadership Development Trainee
Alphabe Insight Inc
Houston, TX, United States Onsite entry Direct
Life Skills Clinician - School-Based
Jane Pauley Community Health Center, Inc.
Indianapolis, Indiana, United States Flexible Direct
After School Instructor (26-27 SY)
KIPP
San Francisco, CA, United States Onsite entry Direct
Leadership Development Associate
Alphabe Insight Inc
Houston, TX, United States Onsite entry Direct
School Counselor - 2026-2027 School Year
River Rock Academy
Middletown, PA Onsite Direct
Counselor-Middle School (2025-2026 School Year)
Christa McAuliffe K-8 Academy Onsite Direct
Director of School and Services
New Story Schools
Wyoming, PA Director Direct
High School Art Teacher
Belmont Charter Network
Philadelphia, Pennsylvania, United States Onsite Junior Direct
Sales Leadership Rotational Program
US Flexible Entry Direct
Middle School Math Teacher
ACCEL Schools
Columbus Arts & Technology Academy Onsite Direct
Lower School Leave Replacement Teacher
New York, NY Onsite Direct
High School Program Associate (2026 -2027)
East Harlem Tutorial Program
New York, New York, United States Onsite Direct
Counselor-Elementary (2026-2027 School Year)
Earhart Environmental Magnet Elementary School Onsite Direct
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- How many school leadership jobs in chicago are available?
- JobsGlitch lists active school leadership jobs in chicago sourced directly from company ATS platforms — not reposted from LinkedIn.
- Are these School Leadership roles actually hiring in Chicago?
- Yes — every listing is indexed directly from company career pages (Greenhouse, Lever, Workday, Ashby). These are not aggregated from other job boards, so they reflect live hiring intent.
- What skills do School Leadership jobs in Chicago require?
- Required skills vary by employer and seniority. Browse the listings above to see the specific requirements for each open role.
- How do I apply for school leadership jobs in chicago?
- Click any job listing to view the full description and apply directly on the company's career page. Upload your resume on JobsGlitch first to see your match score before applying.