Headmaster

Chesterton Academy of St. Carlo Acutis is a Catholic classical high school that will open in the fall of 2026 in Grand Junction, Colorado. This school seeks a founding Headmaster to foster a joyful, faith‑filled academic environment that implements the Chesterton Schools Network curriculum while launching the Academy in its early years.

Headmaster’s Role

The Headmaster serves as the educational leader, responsible for managing policies, regulations, and procedures to ensure a safe learning environment that adheres to our Catholic identity and meets approved curricula. The Headmaster leads curriculum, instructional leadership, hiring and supervision of personnel, student life, discipline, and parent communication.

The Headmaster must be a practicing Roman Catholic, possess a minimum of a Master’s Degree in Administration or related field, and demonstrate commitment to Catholic secondary education. Salary is competitive. The Board of Directors appoints the Headmaster. A collaborative relationship between the Headmaster and Executive Director is required. In addition to any teaching responsibilities, the duties include: (1) curriculum and academic excellence;

(2) instruction; (3) student life and discipline; (4) parent communications; (5) student admissions; (6) guidance; (7) other school operations.

Primary Duties Curriculum and Academic Excellence

• Oversee adherence to Chesterton Schools Network curriculum
• Oversee implementation of changes to curriculum
• Review results of student tests (CLT, PSAT, ACT, SAT)
• Oversee school accreditation process and renewal per Network guidelines

Instruction

• Oversee faculty hiring, evaluation, rehires, terminations
• Conduct classroom observations for faculty members as part of the evaluation process

Student Life and Discipline

• Ensure discipline policies are enforced and communicated
• Oversee parent‑led sports and extracurricular activities
• Ensure effectiveness of virtue house and faculty mentor programs
• Oversee academic and behavioral eligibility for extracurricular activities

Parent Communications

• Send weekly Headmaster Missive to parents or school newsletter
• Meet with parents regarding student discipline and academic issues

Admissions

• Admit new students upon review of placement exam, student application materials, and meeting
• Oversee transfer student process (curriculum, regulations, forms, financial)
• Review placement tests and contact parents with remedial needs
• Deliver presentations to prospective parents and students at selected school events

Guidance

• Coordinate standardized testing, college applications and transcript preparation
• Communicate with colleges, universities and other post‑high school programs
• Promote various vocational opportunities

Other School Operations

• Oversee selection and evaluation of vendors (software, textbooks, other services)

Teaching Responsibilities

• As needed

Relationships

• The Headmaster reports directly to the Board of Directors.
• The Headmaster maintains a consultative, collaborative relationship with the Executive Director.
• The Headmaster maintains a supervisory relationship with faculty and other selected staff, including Administrative Dean and Academic Dean.

Growth and Recruitment

• The Headmaster will possess the leadership qualities to facilitate the scaling of the school to its ideal size and vision.
• The Headmaster will oversee and promote the recruitment of students, faculty, and staff.
• The Headmaster will demonstrate a commitment to the expansion of the school's processes and systems.

Requirements

• Applicant must be a practicing Roman Catholic
• The Headmaster must be passionate about their Catholic faith and demonstrate a deep commitment to classical education.
• Strong communication skills
• Strong leadership skills
• Masters in Education or related field
• Certification:
  Not Required

Experience

• Significant teaching experience in a classical school environment; previous experience in secondary school administration; familiarity with the mission of Chesterton Academy and the teachings of the Catholic Church; and working knowledge of institutional advancement/fundraising.

About Chesterton Academy

Founded in 2008 as a result of a grass‑roots movement of parents, Chesterton Academy offers a rigorous, integrated high school curriculum centered on the Incarnation of Jesus Christ. Focusing on the classics, the school develops complete thinkers who learn to draw on faith and reason for the purpose of building a culture of life. Learn more about Chesterton Academy and the growing national Chesterton Schools Network.

About

the Employer

Inspired by Saint Pope John Paul II, we take as our motto Cultura Vitae
, the culture of life. 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 cultivation of Christian virtues and an appreciation of beauty.

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