Top 20 Head of school Jobs in Windermere Fl

Head of School
The Christ School —Orlando, FL
- Doctoral degree
- Master's degree
- Children
Quick Apply
Head Tennis Coach (JV & Varsity)
Family Christian Center School —Clermont, FL
- Seasonal
- School experience
- CPR Certification
- First Aid Certification
Quick Apply
Head of Finance
Lake Mary Preparatory School —Lake Mary, FL
- From $85,000 a year
- Full-time
- Background check
- School experience
- Microsoft Excel
- Health insurance
- Dental insurance
Quick Apply
Supplement-2026-2027-Competition Cheer-Head Coach
School District of Osceola County —Kissimmee, FL
- Part-time
- High school
- High school diploma or GED
- Public school
Supplement-Girls-Cross Country-Head Coach
School District of Osceola County —Kissimmee, FL
- Part-time
- High school
- High school diploma or GED
- Public school
4d
Supplement-Boys Cross Country-Head Coach
School District of Osceola County —Kissimmee, FL
- Part-time
- High school
- High school diploma or GED
- Public school
4d
Supplement-2026-2027-Boys Soccer-Head Coach
School District of Osceola County —Kissimmee, FL
- Part-time
- High school
- High school diploma or GED
- Public school
Supplement-Softball-Head Coach-Varsity
School District of Osceola County —Kissimmee, FL
- Part-time
- High school
- High school diploma or GED
- Public school
Lay Coach - Head Wrestling Coach
Lake County School District (FL) —Groveland, FL
- $1,540 - $1,650 a month
- Background check
- CPR Certification
- High school
Supplement-Softball Head Coach
School District of Osceola County —Kissimmee, FL
- Full-time
- High school
- High school diploma or GED
- Public school
3d
Supplement-2026-2027-Girls Soccer-Head Coach
School District of Osceola County —Kissimmee, FL
- Part-time
- High school diploma or GED
- Public school
- Middle school
JV Girls Basketball Head Coach
Cristo Rey Orlando High School —Orlando, FL
- Weekends as needed
- School experience
- Spanish
- CPR Certification
- 403(b)
Quick Apply
3d
JV Boys Basketball Head Coach
Cristo Rey Orlando High School —Orlando, FL
- Weekends as needed
- School experience
- Spanish
- CPR Certification
- 403(b)
Quick Apply
3d
JV Girls Soccer Head Coach
Cristo Rey Orlando High School —Orlando, FL
- Weekends as needed
- School experience
- Spanish
- CPR Certification
- 403(b)
Quick Apply
3d
Head Boy's Varsity Soccer Coach
Orangewood Christian School —Maitland, FL
- Background check
- School experience
- CPR Certification
Quick Apply
Girls Lacrosse Head Coach
Orangewood Christian School —Maitland, FL
- Part-time
- Background check
- Mid-level
- Organizational skills
Quick Apply
JV Boys Soccer Head Coach
Cristo Rey Orlando High School —Orlando, FL
- Weekends as needed
- School experience
- Spanish
- CPR Certification
- 403(b)
Quick Apply
3d
Head Custodian
Bridgeprep Academy, Inc. —Saint Cloud, FL
- $16 - $18 an hour
- Background check
- Classroom
- Ability to walk for extended periods
Quick Apply

Other jobs to consider

Find your next job by exploring related positions.

Land Survey Technician/ Party Chief Job Opportunity in Orlando, FL
Allpoints Land Survey —Orlando, FL
Familiarity with CAD software for creating detailed survey drawings Understanding of GIS applications for spatial data analysis.
Quick Apply
10d
SLAB Crew Chief
M.T. Constructors —Orlando, FL
Reliable transportation and a valid driver's license. OSHA certification is a plus. Do you have a valid Driver's License? Train and mentor crew members.
$25 - $35 an hour
Quick Apply
4d

Show more related jobs

Explore jobs in cities nearby

Check out jobs in cities near your current location, Columbus

CHIEF ACADEMIC OFFICER
Columbus City Schools —Columbus, OH
Directs the development, implementation, and monitors a comprehensive and aligned curriculum management system based on federal and state mandates and district…
$158,854 a year
Head Cook - Middle School
Whitehall City Schools —Whitehall, OH
Meet standards of cleanliness and sanitation for the food preparation area as set by state and local standards. A high school diploma, GED, or equivalent.
8d

Show more jobs in cities nearby

I want to receive the latest job alert for head of school in windermere fl

By signing in to your account, you agree to SimplyHired's Terms of Service and consent to our Cookie and Privacy Policy.

Head of School

The Christ School -
Orlando, FL

Quick Apply

Job Details

Qualifications

Master's degree

Full Job Description

Head of SchoolThe Christ School | Orlando, FloridaPosition Announcement – May 1, 2026

About The Christ School

The Christ School (TCS) seeks a Head of School to lead the school into its next chapter of growth and development.

Founded in 1996, TCS is an independent, interdenominational Christian school serving 435 families and 560 students from transitional kindergarten through 8th grade. TCS is located in the heart of downtown Orlando on the campus of First Presbyterian Church, with whom it enjoys a strong and valued partnership.

Accredited by the Florida Council of Independent Schools (FCIS), Cognia, Christian Schools of Florida (CSF), and the Council on Educational Standards and Accountability (CESA), TCS delivers a rigorous academic program grounded in a distinctly Christian worldview.

A hallmark of TCS is The Bridge Program, which currently serves 86 students with dyslexia. The Bridge Program is one of only 18 schools in the country accredited by the Orton-Gillingham Academy and is the only program of its kind in the state of Florida.

The Christ School operates with an open enrollment philosophy and has experienced significant growth in recent years. The school benefits from a dedicated faculty, engaged families, and vibrant student community.

The Opportunity

The Board of Trustees seeks a mission-driven and experienced leader to serve as Head of School and lead The Christ School into its next chapter of impact and growth. This is a unique opportunity to lead a healthy, well-established Transitional K–8 school while thoughtfully preparing for long-term growth, including the potential expansion to a Transitional K–12 model and the evaluation of future campus needs. The Board is committed to a disciplined and sustainable approach to growth that builds on the school’s existing strengths, culture, and community.

Position Overview

The Head of School serves as the academic and spiritual leader of TCS and reports directly to the independent Board of Trustees.

The successful candidate must be comfortable strengthening day-to-day operations and investing in people and culture while also providing strategic, visionary leadership to advance its mission, culture, and guide long-term planning efforts.

Key Responsibilities

Articulate and advance a clear, compelling vision that reflects and strengthens the school’s Christian mission
Lead, inspire, and develop faculty and staff to support excellence in both academic achievement and spiritual growth
Partner closely with the Board of Trustees to execute strategic priorities, including long-term planning for campus needs, growth, and potential expansion or relocation
Strengthen and steward relationships with families, church partners, and the broader school community
Ensure strong operational leadership across key functions, including enrollment management, financial sustainability, and advancement
Deepen and sustain the partnership between The Christ School and First Presbyterian Church
Champion a family-centered approach that delivers an individualized, Christ-centered educational experience
Foster a culture of trust, transparency, and effective communication across all constituencies
Cultivate a collaborative, positive, and mission-driven school culture that attracts and retains exceptional talent

Qualifications & Attributes

The next Head of School will:

Demonstrate a genuine love for children and a deep commitment to supporting and partnering with their families
Bring experience leading institutional growth, expansion, or increased organizational complexity
Demonstrate success in enrollment management and long-term financial sustainability
Possess the ability to lead effectively through change, with clarity, steadiness, and strong communication
Maintain a disciplined approach to financial stewardship and overall organizational health
Exhibit a personal and authentic commitment to the mission of Jesus’ Church
Appreciate and honor the history, culture, and traditions of The Christ School
Understand and embrace the unique opportunities and dynamics of the Central Florida community
Lead from a biblical perspective, integrating faith into decision-making while casting a clear vision for spiritual formation and discipleship
Be drawn to an open enrollment philosophy
Hold a master’s degree from an accredited institution (doctoral degree preferred)

Compensation

The Board is prepared to offer a highly competitive compensation package aligned with top independent schools of similar size and scope.

Application Process

Applications, nominations, and expressions of interest will be accepted until a Head of School is appointed.

For full consideration, candidates should submit:

A letter of interest
Curriculum vitae or resume
A statement articulating personal Christian faith and practices
Three professional references

Materials should be addressed to the Head of School Search Committee and submitted to:[email protected]

Confidential inquiries and questions may be directed to the Head of School Search Committee, Attn: Chrissy Ford.

Learn MoreFor additional information about The Christ School, please visit: thechristschool.org

Equal Opportunity Employer

The Christ School is an equal opportunity employer.

Quick Apply

Refine Your Search

head of school jobs in windermere fl

Head of School

Head Tennis Coach (JV & Varsity)

Head of Finance

Supplement-2026-2027-Competition Cheer-Head Coach

Supplement-Girls-Cross Country-Head Coach

Supplement-Boys Cross Country-Head Coach

Supplement-2026-2027-Boys Soccer-Head Coach

Supplement-Softball-Head Coach-Varsity

Lay Coach - Head Wrestling Coach

Supplement-Softball Head Coach

Supplement-2026-2027-Girls Soccer-Head Coach

JV Girls Basketball Head Coach

JV Boys Basketball Head Coach

JV Girls Soccer Head Coach

Head Boy's Varsity Soccer Coach

Girls Lacrosse Head Coach

JV Boys Soccer Head Coach

Head Custodian

Other jobs to consider

Explore jobs in cities nearby

I want to receive the latest job alert for head of school in windermere fl

Explore jobs in more locations

Job Seeker Tools

Employer Tools

Browse

Stay Connected