Partner: Chesterton Academy of Orlando

Location:  Orlando, Florida


Chesterton Academy of Orlando is seeking its inaugural headmaster to spearhead the founding of the school. In close partnership with a faithful, well-networked, and highly skilled Board, the headmaster will step onto an already-purchased campus shared with a K-8 classical school, Highlands Latin Academy, with families eager to enroll in a Catholic, classical community that develops faith and reason in students to allow them to discover their God-given talents and to discern their ultimate calling with joy.

No other classical high school grounded in the Catholic tradition exists in the Greater Orlando area. Chesterton Academy is located in the Orange/Seminole county area in Winter Park and is ready to open its doors for the 2022-2023 school year. Founded by a grassroots movement of families in the area, the Academy has already secured significant donations and has a fundraising plan in place. The school now seeks a leader devoted to the faith, committed to classical curriculum and pedagogy, and ready to build a culture of life.


Chesterton Academy of Orlando Snapshot


To prepare students to triumph over the materialism and despair that pervade our culture and to accept our Lord’s offer to have life and have it abundantly.


To graduate students who believe they are a beloved child of God, are fully alive in their faith, and are drawn to a good life of joy, intelligence, and virtue.


  1. Intellect—the classics of Western thought from physics to philosophy; the interrelationship of the great ideas; teaching students not merely what to think but how to think.
  2. Character—students grow in the four cardinal virtues of prudence, temperance, fortitude, and justice, which are the foundations of leadership.
  3. Spirituality—students come to understand and embrace the truth of why they exist: to know, love, and serve God in this world and to be happy with Him forever in the next.


TYPE: Private (affiliated with Chesterton Schools Network)



Key Qualifications 

The headmaster must embody the school’s pillars of formation in intellect, character, and faith. The ideal candidate has a relevant graduate degree, school administrative leadership experience, and classical teaching experience, as well as firm understanding of the teachings of the Catholic Church. He or she will also:

  • Have 10+ years professional experience with at least five years senior management/administrative experience.
  • Strongly prefer Catholic, classical philosophical underpinnings and approach.
  • Cast a compelling and persuasive vision for the classical Catholic educational model.
  • Be a figurehead, spokesman, and spiritual leader.
  • Be strategic and decisive in long-term planning and program development and other matters related to the school’s growth and culture.
  • Have a strong ability to manage conflict and lead with boldness and enthusiasm.
  • Demonstrate superior written and verbal communication.
  • Have some working knowledge of institutional advancement/fundraising.



The headmaster at Chesterton Academy of Orlando will adopt the missionary spirit of the founders, who seek to provide an integrated high-school curriculum centered on Christ’s Incarnation.

This time is a pivotal one for prospective families; it requires a sharp leader who is determined to bring into existence an exceptional educational community that would be otherwise unavailable in Orlando.

But this opportunity is also a challenge. The work ahead requires a leader with a robust vision for Catholic education—one who is ready to tackle difficult topics and decisions with faithful discernment, all the while overseeing and protecting the hearts and minds of students.

Ultimately, the headmaster helps to create and preserve a joyful learning environment that cultivates virtue and teaches students to embody truth, goodness, and beauty.

The headmaster’s primary responsibilities include:

  1. LEADERSHIP AND MANAGEMENT—oversee all employees, admissions, operations and facilities; attract and retain talented staff; educate families and staff; and ensure compliance with all legal and ethical procedures running the daily operations of the school.
  2. STRATEGIC PLANNING AND GROWTH—draft and lead short- and long-term strategic plans for increasing enrollment, curriculum development, campus planning, and other strategic objectives.
  3. SCHOOL CULTURE AND COMMUNITY—foster the school’s classical and Catholic culture, develop faculty with a classical pedagogical approach, lead activities to form members in the virtues of the culture, and safeguard the community by ensuring all members understand and embrace the pillars of the school.
  4. FINANCIAL STABILITY—support the fundraising and marketing efforts of the school, develop strong donor relations and communications, increase revenue and operate within approved budgets, and exercise accurate financial oversight.
  5. BOARD GOVERNANCE—communicate effectively with the Board, provide regular and timely reports to ensure compliance with by-laws, and implement the vision set for the school.

Chesterton Academy of Orlando seeks an inaugural headmaster to establish a robust classical high school and foster its mission to develop students who know, love, and serve God.

The headmaster will be assisted in this work by an exceptionally talented Board that is committed to the school’s success. Chesterton Academy’s board includes founders of large, successful companies, a lawyer who works in the state capital, a senior executive at a premier Catholic evangelical ministry, and people with advanced degrees and professional experience in education and logistics. The Board has already completed a five-year financial plan to assist the headmaster in projecting revenues, expenses, personnel, and fundraising needs. It is committed to securing the entire operating cost of each school year prior to the school year beginning. With robust support from the Board of Directors, the headmaster can strategically increase enrollment, strengthen culture, and lead the only classical high school, taught from a Catholic perspective, in the Orlando area.



Inspired by Saint Pope John Paul II, Chesterton Academy schools take as our motto Cultura Vitae, the culture of life. We are named after G.K. Chesterton, the model of a complete thinker and modern defender of the faith. We make it our mission to prepare our students to triumph over the materialism and despair that pervade our culture and to accept our Lord’s offer to have life and have it abundantly. Our classical curriculum combines a broad, liberal arts education with a strong emphasis on the development of Christian virtues and an appreciation of beauty.

The school’s founding is a courageous effort to bring truth, goodness, and beauty to young minds and souls.

At the Academy, the headmaster will have the opportunity to be the leader of the Catholic classical education movement in a diocese and city full of families desirous of such formation for their children. Already over 100 families (and over 300 total students) have added their names to the Chesterton Academy interest list. The headmaster’s student recruitment efforts will likewise be immeasurably assisted by the school’s proximity to Highlands Latin Academy, the sister K-8 classical school with which we share a campus.

Chesterton Academy’s location in Orlando likewise offers a particularly hospitable climate for families, with sunny and warm weather year-round and no state income tax. Florida is also a state that is very friendly to educational freedom and private schools: the Florida Empowerment Scholarship provides hundreds of millions of dollars to families for tuition and fees at any private school of their choice—including Chesterton Academy.

By bringing together families who share a commitment to raising their children in the faith and Great Books, the headmaster be at the forefront of challenging the status quo and offer a community that educates the whole person to be happy in this life and the next.

In this postmodern environment, Chesterton Academy of Orlando aims to produce graduates who love God and love reason, speak with humility and wisdom, cherish beauty, embody virtue, and are invested citizens in their communities and wider society—the opportunities in the city it has made its home are endless and waiting for you.

See full job description here.