An exceptional opportunity for an experienced educational leader to drive growth and excellence as Head of School at Windermere Preparatory School, a leading international day and boarding school in Orlando, Florida.

For further information you can view the candidate brochure here.

THE SCHOOL

With our well-landscaped 48-acre campus spread across the Windermere area of Orlando, Florida, Windermere Preparatory School is an international day and boarding school with extraordinary academic experiences, global passions, and local presence. Our school is home to 350 staff members and is made up of 1,675 students across 55 nationalities spanning the Early Years and all of K–12 education. We offer a wide range of academic programs, including the International Baccalaureate (IB) Diploma Programme and a unique high school concentration program with tracks for fine arts, STEM, and social impact and leadership.

Situated next to Lake Cypress of the Butler Chain of Lakes, our vibrant campus has refreshing pools of lake water and green spaces all integrated to our Lower, Middle, and High School academic buildings, athletic facilities, the Cypress Center for the Arts, residential townhouses, and more. We holistically emphasize components of intellectual, personal, emotional, and social growth through many resources and extracurricular activities. 

As the Head of a school that is part of the Nord Anglia Education family, you’ll lead with global reach and local impact. Our unique collaborations with Juilliard, MIT, UNICEF, IMG Academy and King’s College London, along with access to our Global Campus, create extraordinary opportunities for students and staff alike.

WHY LEAD WITH NORD ANGLIA?

At Nord Anglia, the Head of School is central to each school’s success. We carefully match leaders to the unique character and needs of each school, ensuring you’re set up to thrive. You’ll have the autonomy to lead your school your way, while operating within a clear framework of expectations that drive excellence across student outcomes, financial performance, marketing, and stakeholder engagement.

This transparency of purpose is a strength: you’ll know exactly what success looks like and be supported to achieve it. You’ll be part of our global senior leadership team, collaborating with fellow Heads of School in your region and across our network to share best practice and elevate your school’s offer.

From day one, you’ll benefit from:

• Regional support teams and peer networks.
• The Principal In Role Support (PIRS) programme, including knowledge and support alongside other new Principals. executive coaching and peer to peer mentoring.
• Extensive professional development via Nord Anglia University, including leadership programmes, global conferences, and tailored learning pathways.
• Competitive salary, performance-based bonuses, health insurance, relocation assistance and schooling for your children.
• The possibility of career progression across school, regional and global leadership roles.

WHO WE’RE LOOKING FOR

As an established American boarding and day school, Windermere Preparatory School is entering an exciting phase of significant growth and expansion, including opportunities for new developments and facilities. We are therefore seeking a Head of School who combines a deep understanding of the American educational and boarding school context with strong commercial acumen and the ability to drive strategic growth. As an IB continuum school, knowledge of the IB curriculum and experience within an international educational environment are desirable, alongside an appreciation of the unique strengths and expectations of American schooling.

The ideal candidate will:

• Have a Master’s degree in education, educational leadership, or related field
• Bring significant senior leadership experience in K-12 education with experience of working in large complex schools.
• Have an understanding of the US market.
• Have experience in a boarding setting, with a strong track record of delivering academic excellence and whole-school improvement.
• Bring a passion for international education and preferably experience of working with the IB curriculum.
• Bring commitment to safeguarding and child protection, with in-depth experience of how to build and maintain a strong safeguarding culture in line with statutory requirements and international best practices.
• Have experience in expansion and exponential growth is desired.
• Demonstrate an ability to lead and develop high-performing teams, fostering a positive and inclusive culture focused on continuous professional growth, talent development, and staff wellbeing.
• Have strong commercial and strategic acumen, including experience managing budgets, resources, and performance metrics to support the school’s long-term success and sustainability.
• Be a persuasive storyteller and connector, with the ability to engage and influence a wide range of stakeholders (students, staff, parents, and the wider community) and act as a compelling ambassador for the school.

Start Date: August 2026

Application Deadline: 26th October 2025

Interviews: week commencing 1st December 2025

At Nord Anglia Education we are committed to providing a world-class, safe, happy environment in which children and young people can thrive and learn. We are committed to safeguarding and promoting the welfare of all our pupils where we embrace all races, abilities, religions, genders, and cultures.

All post holders in regulated activity (having regular unsupervised contact with children) are subject to appropriate national and international vetting procedures including satisfactory criminal record checks from both your country of residence/birth and any country of residence within the last 10 years.

We welcome applications from suitable qualified persons from all diverse backgrounds.

Applicants must be currently authorized to work in the United States on a full-time basis. We are not able to sponsor or assume sponsorship of employment visas.