Founding Headmaster Position
POSITION DESCRIPTION
Founding Headmaster
Reports to: Board of Trustees
Download Headmaster Position Description
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
The Headmaster exercises leadership in the following domains:
CATHOLIC CULTURE
Fully embrace and support the school’s mission in word and deed, modeling through personal example a life of prayer and fidelity to the teachings of the Catholic Church
Oversee teacher and student faith formation through liturgical and sacramental opportunities, retreats, etc.
Ensure that Catholic doctrine is being upheld throughout all aspects of the school’s curriculum, policies, and programming
Develop positive relationships with local clergy and religious who support the school’s mission
CURRICULUM AND ACADEMIC EXCELLENCE
Understand, support, and promote the vision of the Chesterton Schools Network curriculum
Ensure teachers are trained, prepared, and equipped to implement the Chesterton Schools Network curriculum with all necessary materials and resources
Participate in Chesterton Schools Network curriculum discussions and headmaster calls
Review grade books and ensure faculty are current on inputting grades and returning graded work to students
Promote intellectual virtue, academic integrity, and academic excellence within the school community
Promote the Franciscan University of Steubenville Academic Partnership with our current and prospective families
TEACHER FORMATION
Oversee faculty hiring, management, evaluation, rehires, terminations, and teaching assignments
Cultivate a faculty of friends through thoughtful professional development programming that helps faculty grow in their own learning, their understanding of Catholic classical pedagogy, and their appreciation of the spirit of G.K. Chesterton
Meet with teachers regularly to address issues of pedagogy and instruction, such as pacing, adherence to the curriculum, workload, classroom management, and goal-setting.
Conduct frequent classroom observations of faculty members as part of their evaluation process
STUDENT LIFE AND DISCIPLINE
Ensure disciplinary policies are consistent with the school's mission of forming joyful disciples of Christ
Annually review and update the family handbook
Oversee extracurricular activities and athletic programming, ensuring quality and fidelity to the school’s mission
Ensure effectiveness of the Chesterton house system
PARENT PARTNERSHIPS
Distribute a weekly newsletter communication to parents
Establish policies and protocols for communication with parents regarding student progress and behavior
Promote and uphold the school’s disciplinary, uniform, and academic policies
Create effective community programming that engages parents in the life of the school
ADMISSIONS, ENROLLMENT, AND DEVELOPMENT
Actively engage in the recruitment of new students through participation in admissions events
Work with the admissions team to review prospective student applications
Deliver presentations to prospective parents and students at open houses and selected school events
Assist the Board of Trustees with fundraising and donor relations through participation in fundraising events
TEACHING RESPONSIBILITIES
Teach up to two classes within the Chesterton curriculum
Serve as primary substitute teacher in case of teacher absences
OTHER ADMINISTRATIVE RESPONSIBILITIES
Ensure safety of and supervises use of school grounds and facilities, developing emergency preparedness plans, and liaising with building owner to ensure facility upkeep
In consultation with the Board of Trustees, develop and administer a school budget, supervise school finance, and monitor expenditure of funds
Relationships within the Administrative Model
The Headmaster maintains the following working relationships:
The Headmaster is hired by and reports directly to the Board of Trustees.
The Headmaster is a part of and works closely in collaboration with the school’s growing executive team.
The Headmaster has a supervisory relationship with the faculty and staff.
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:
Bachelor’s degree (Master’s preferred);
Teaching experience (classical school environment preferred);
Experience in secondary school leadership or administration (preferred); and
Familiarity with the mission of Chesterton Academy of the Immaculata and the teachings of the Catholic Church.
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.