Founding Headmaster

Reports to: Board of Directors

ABOUT THE SCHOOL

Chesterton Academy of Fredericksburg is a classical high school in the tradition of the Catholic Church and a member of the Chesterton Schools Network (CSN), opening in Fall 2027. Our integrated curriculum, provided by CSN (a canonically approved lay apostolate of the Society of G.K. Chesterton), is centered on the Incarnation of Jesus Christ and grounded in the classics. It forms complete thinkers who draw on faith and reason to build a culture of life.

THE ROLE

The founding Headmaster will shape the academic and spiritual culture of a new school. The Headmaster implements the school's mission and the CSN curriculum, hires and forms the founding faculty, and leads the formation of the whole student. During these founding years, the Headmaster works directly with the Board, which carries fundraising, marketing, and business responsibilities, and plays an active part in recruiting and welcoming families. Because the founding Headmaster will hire our first faculty and prepare the school for opening, this position needs to be filled well before Fall 2027.

RESPONSIBILITIES

• Founding the school: recruit, hire, and train the founding faculty using CSN hiring practices; build the academic calendar and bell schedule, including students' attendance at Mass at St. Mary's Catholic Church; establish academic and discipline policies, handbooks, and systems; and guide the school through CSN accreditation.
• Curriculum and academic excellence: implement the CSN curriculum through Chesterton Online; ensure teachers use the proper materials; take part in CSN headmaster calls and training; oversee student testing and use the results to strengthen instruction.
• Faculty leadership: oversee hiring, evaluation, teaching assignments, and renewals; meet regularly with teachers on pacing, curriculum adherence, homework load, and classroom management; conduct at least one formal and one informal observation of every teacher each year; and help faculty cultivate a Socratic, Chestertonian classroom.
• Student formation: uphold discipline and uniform policies, establish the House system, and nurture the intellectual, spiritual, and character formation of every student.
• Families and admissions: present at open houses and information nights, interview prospective students and families, help families understand school policies, ensure teachers communicate regularly with parents, and protect family life by keeping workloads reasonable.
• Teaching: teach up to two classes, based on the school's needs and the Headmaster's background.

REQUIREMENTS

• Practicing Roman Catholic, faithful to the Magisterium and willing to take the Oath of Fidelity
• Bachelor's degree required; graduate degree preferred
• Secondary teaching experience; classical school experience preferred
• School leadership or administrative experience, or clear evidence of leadership ability
• Familiarity with and enthusiasm for classical education and the Chesterton Schools Network model
• Completion of Safe Environment training and a background check

COMPENSATION

$75,000+ per year, including some teaching duties, depending on experience.

START DATE

End of 2026 preferred. Because we are building a new school, we need our founding Headmaster hired and in place well ahead of our Fall 2027 opening.

TO APPLY

Send a cover letter, resume, statement of educational philosophy, and three references (including one former supervisor) to [REMOVED - SEE ORIGINAL LISTING] A one- to two-page vision for the school's first three years is welcome. Applications will be accepted through November 20, 2026.