Headmaster - Chesterton Academy of St. Pier Giorgio Frassati

Job Description

As Headmaster of CASPGF, you will be building on the previous four years of foundational work to lead the school to the next level of joyful operational excellence and incarnational education. You will be clearly presenting the vision of developing complete thinkers through classical education who draw on faith and reason to excel in college, career, family life, and of service to Christ our Lord. You will lead our teachers in adherence to our school policies and thereby create an environment that attracts and retains students and families.

WHAT YOU'LL LOVE:
• Living an integrated life where your Catholic faith is at the center of your work building a joyful, incarnational learning environment. Leave the chaos of modern education behind and put your heart into what you always wanted teaching to be about.
• Working with students who are eager to learn and who ask the great questions of life's meaning and purpose. There are no cell phones in school and no student computers in class so that the students can be fully engaged in the material and support each other in the wonderous search for truth, goodness, and beauty.
• The excitement of moving our school from the downtown Portland area to a new location at St. Joseph the Worker on the east side of Portland, an area that has not had a Catholic high school.
• Running an independent Catholic classical high school in partnership with the Chesterton Schools Network (CSN); the CSN is there to help by supplying a structured curriculum with daily lesson plans, marketing materials, training, ongoing support, and more.
• The opportunity to develop your career with ICLE (Institute for Catholic Liberal Education) programs, one of which has its in-person meetings in Portland.
• The beauty of living in the Pacific Northwest with mild climate, endless outdoor activities such as year-around skiing, vibrant neighborhoods and suburbs, cultural events including the William Byrd Festival, and a strong Catholic community.
• A supportive, small school environment for you to grow into the special skills of a Chesterton headmaster.
• Chesterton Schools Network Summit conference June 22-26, 2026 at Ave Maria University.

WHAT YOU'LL DO:
• As headmaster, you will be responsible for implementing the school's academic vision and mission, both strategically and in day-to-day operations. As such you will report directly to and collaborate with the Board of Trustees.
• Collaborate with the Board to coordinate activites needed for a successful school.
• Create an encouraging environment that attracts and retains students and families.
• Ensure joyfully Catholic spritual formation for our students utilizing CSN guidelines.
• Responsible for the hiring, inspiring, evaluation, training and developing of our teachers.
• Oversee adherence to the CSN curriculum and ensure that classes are academically rigorous.
• Strive to conduct weekly 1-1 meetings with each teacher covering at least the following: adherence to the curriculum, homework load, classroom management and professional development. Ensure that teachers understand and adhere to school policies.
• Conduct classroom observations as part of evaluation process; also arrange for master teachers and school leaders to conduct observations. May teach 2-4 classes while the school is growing. Help faculty to cultivate truly Socratic classrooms.
• Participate in student recruitment, especially by developing a welcoming, effective shadow day program. Create fun events for prospective students and parents, and give presentations as needed for school events and open houses.
• Build strong parent-school relationships and promote enthusiasm for classical education among our parents. Ensure that teachers communicate regularly with parents and review homework load.
• Promote and ensure that standardized tests are administered, especially the CLT (Classic Learning Test). Utilize the results to improve our instructional process.

WHAT YOU OFFER - YOUR SKILLS, MISSION FIT AND PASSIONS:
• Must be a practicing Roman Catholic in full communion with the teachings of the church and demonstrate a commitment to Catholic secondary education; must take the Oath of Fidelity to the Magisterium.
• An appropriate Master's degree or higher (or equivalent applicable experience) preferred.
• 3+ years of experience classroom teaching and/or administration.
• Teaching experience in a classical school or educated in a great books environment preferred.
• Teaching certificate, management or fund-raising experience are valued.
• Excellent leadership skills and excellent ability to organize, plan and set job priorities.
• Strong communication skills, both in personal interactions and for large groups.

About the Employer

Our mission is to raise up a new generation of joyful leaders and saints educated in the classical tradition and truths of the Catholic faith. Our goal is to combine the highest levels of academic excellence with forming the whole student through Catholic spiritual formation in faith, hope and charity. Intellectually, our integrated curriculum teaches our students not merely what to think but how to think. Faith and reason meet in every class. In the words of G. K. Chesterton, "there is a whole truth of things, and that in knowing and speaking it we are happy."