Website Chesterton Academy of the Rogue Valley Central Point, Oregon

Chesterton Academy of the Rogue Valley is a joyful, classical high school, rooted in the Catholic faith. We are seeking a talented, dynamic, and passionate leader to serve as full-time Headmaster starting in the 2024-25 academic year. We offer a competitive salary and a faith-filled, Catholic environment.

The Headmaster serves as the educational leader of Chesterton Academy of the Rogue Valley. He or she will be responsible for fostering a safe learning environment; nurturing a joyful culture of life; promoting and adhering to our Catholic identity; and overseeing the implementation of approved curricula and mission of the school. He or she will be responsible for developing and maintaining a positive working relationship with the pastor, parish staff, and parish community.

The Headmaster works alongside the Executive Director to provide cultural and administrative leadership to the school. The Headmaster reports to the Board of Directors. Together they share the responsibilities of nurturing and maintaining the mission and traditions of the school, as well as ensuring fidelity to the Magisterium of the Catholic Church.


Primary Responsibilities and 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 Chesterton Schools Network guidelines.



·       Teach 2-3 courses in addition to routine Headmaster duties.

·       Oversee faculty hiring, evaluation, mentoring, and training.

·       Conduct classroom observations as part of the faculty evaluation process.


Student Life and Discipline:

·       Persevere in focusing on the formation of the whole student.

·       Ensure discipline policies are communicated and enforced.

·       Oversee extracurricular activities. We do not yet have an established athletics program, but desire to grow one or more over time. We are an OSAA Associate Member school which enables our students to participate in athletics with partner school athletics.

·       Ensure the effectiveness of virtue, house, and faculty mentor programs.

·       Oversee academic and behavioral eligibility for extra-curricular activities.


Parent Communications:

·       Regularly communicate with parents and supporters in-person, via email, or by phone on topics related to school progress.

·       Meet with parents regarding student discipline and academic issues.

·       Contribute information to the weekly Newsletter.



·       Ignite support and enthusiasm for classical education among faculty, parents, and stakeholders.

·       Leverage position to play a crucial role in recruiting and retaining both students and faculty.

·       Participate in fundraising events, often as a key speaker.



·       Admit or deny new students upon review of placement exam, student application materials, and interview.

·       Oversee the transfer student process (curriculum, regulations, forms, and financial).

·       Review placement tests and contact parents with remedial needs.

·       Deliver presentations to prospective parents and students at selected school events.


Job Requirements:
·       Must be practicing Roman Catholic and demonstrate a commitment to Catholic secondary education (Required)

·       Bachelor’s Degree (Required)

·       Master’s Degree (Preferred)

·       4+ years of experience in secondary school teaching or administration (Preferred)

·       2+ years teaching experience in a classical school environment (Preferred)

·       1+ years of experience overseeing non-profit or for-profit fundraising (Preferred)

·       Exemplary verbal and written communication skills (Required).

·       Resilient and adaptable with strong time management and organizational skills.

·       Background check to work with minors (Required)

·       Committed to the mission of Chesterton Schools Network and the teachings of the Catholic Church.


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. See more at and


About the Employer:

* Chesterton Academy of the Rogue Valley is a classical high school in the Catholic tradition located in Central Point, Oregon. The school is collocated with Shepherd of the Valley Catholic Church in Central Point, Oregon.

* Chesterton Academy of the Rogue Valley offers an integrated, rigorous curriculum centered on the Incarnation of Jesus Christ. Our school focuses on the classics. We school develops complete thinkers who learn to draw on faith and reason for the purpose of building a culture of life.

* Our school opened in 2023 with both freshmen and sophomore classes. As part of our school’s growth, we will add a junior class in 2024, and senior class in 2025. Our average class size is between 9-12 students.

* We offer a faith-filled environment for students and faculty. We begin each day with singing Lauds; attend noon Mass on Wednesdays, Thursdays, and Fridays;  and on non-Mass days, our school participates in prayer or adoration.



Point of Contact:

Interested candidates should submit a cover letter, resume, and three to five references to Chesterton Academy of the Rogue Valley, c/o Mr. Jon Bates,

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