Headmaster

Job Description

Chesterton Academy of the Immaculata, a co-ed high school in Framingham, MA, serving grades 9-12, seeks a joyful and faithful disciple of Jesus Christ, a skilled educator who has a passion for Catholic classical education, an entrepreneurial spirit and a track record of successful leadership in an academic environment to serve as the Headmaster of our school starting July 1, 2026.

Headmaster's Role
The Headmaster leads the faculty and staff of Chesterton Academy of the Immaculata in bringing the school's mission and vision to life in the day-to-day operations of the school. As guardian of our school's mission and curator of our academic community and culture, the Headmaster plays a crucial role in creating a vibrant and joyful environment that attracts and retains students and families. He/she serves as the lead teacher and leader of our faculty and is responsible for guiding our faculty as they provide a learning environment that is faithful to our Catholic identity, the mission of the school, and the Chesterton Schools Network model and curriculum. He/she plays a key role in the formation of teachers as Catholic classical educators and in inspiring enthusiasm for classical Catholic education in general and for Chesterton Academy of the Immaculata in particular among all stakeholders in our community.

To fulfill these responsibilities, the Headmaster will ideally possess the following characteristics:
Understanding of, enthusiasm for, and skill in implementing the Church's educational mission
Extensive experience as a Catholic classical educator,
Ability to teach most courses in the Chesterton Schools Network curriculum
Exemplary verbal and written communication skills
Ability to adapt to challenges with a spirit of magnanimity and good humor
A compassionate heart for service, with empathetic interpersonal and conflict-resolution skills
Enthusiasm for the education and formation of teenage students
Commitment to his/her own intellectual, professional, and spiritual growth and development
Commitment to maintaining a joyful school community and learning environment
A "startup mindset," marked by comfort in fast-paced and evolving environments; willingness to take ownership; ability to create systems and processes; and skill in inspiring faculty and staff to have the same dedication and mindset
Superior organizational skills and attention to detail
A resourceful, innovative, and solution-oriented approach to leadership

Qualifications
The Headmaster must be a practicing Roman Catholic and demonstrate a commitment to Catholic secondary education. He/she must be prepared to take an Oath of Fidelity to the Magisterium of the Catholic Church.

Other qualifications include:
Master's degree (required)
Teaching experience (classical school environment preferred)
Experience in secondary school leadership and administration (required)
Ability to effectively communicate the mission of Chesterton Academy of the Immaculata and the teachings of the Catholic Church (required)
Experience in the setup and administration of school management systems (preferred)
Experience in onboarding staff, negotiating and executing faculty contracts (preferred)
Familiarity with the Boston Catholic education landscape (preferred)

To Apply
Applications should include:
A cover letter explaining how your experience exemplifies the leadership we seek
A curriculum vitae
Three professional references with names, relationship, phone number, and email address
One pastoral reference

Please direct all inquiries and curriculum vitae to the Board Chair, Mrs. Nathalie Calvo at careers@chestertonimmaculata.org.

Salary is competitive and commensurate with experience, and includes comprehensive health benefits.

Start Date: July 1, 2026

Applications received by February 22, 2026, will be given priority consideration. The position remains open until filled.

About the Employer

Chesterton Academy of the Immaculata is a member of the Chesterton Schools Network, sponsored by the G.K. Chesterton Society. chestertonschoolsnetwork.org

Under the patronage of our Blessed Mother, Chesterton Academy of the Immaculata seeks to partner with parents in forming young men and women to be joyful leaders and saints. We cultivate Christian virtues and guide students in the pursuit of Truth, Goodness and Beauty. By providing a rigorous, classical, Catholic education faithful to the Magisterium, we inspire our students to be disciples of Christ and bear witness to a culture of life. www.chestertonimmaculata.org