Founding Headmaster

Founding Headmaster
Reports to: Board of Trustees

Chesterton Academy of the Immaculata, a co-ed high school in MetroWest Boston serving grades 9-12, seeks a joyful, faithful disciple of Jesus Christ and 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 founding Headmaster of our school, which will open in September 2025.

The Mission of Chesterton Academy of the Immaculata

Under the patronage of our Blessed Mother, Chesterton Academy of the Immaculata provides an affordable Catholic education that supports parents in raising their children as joyful saints. By providing a rigorous classical education that is faithful to the Magisterium and anchored in the Sacraments, we seek to impart to our students the intellectual, moral, and spiritual wisdom of the Catholic Church. By guiding our students in the pursuit of Truth, Goodness, and Beauty, we seek to form disciples of Christ, set free to bear witness to a culture of life and to live in accordance with their dignity as sons and daughters of God.

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
• Compassionate and empathetic interpersonal and conflict resolution skills
• Enthusiasm for the education of teenage students
• Commitment to his/her own intellectual, professional, and spiritual growth and development
• A positive and energetic approach to his/her responsibilities
• Commitment to maintaining a joyful school community and learning environment
• A vibrant personal prayer life

See full job description here.

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.

Start Date: February 1, 2025

Applications received by October 31st will be given full consideration. The position remains open until filled.