Head of School

Chesterton Academy of Blessed Michael McGivney

New Haven, CT

Job ID#:
15742172015
Posted:
September 30, 2025
Expires:
November 29, 2025
Category:
Secondary Education
Terms:
Part-Time Employee
Experience:
5-10 Years
Education:
Graduate Degree
Base Pay:
Salary
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Job Description

[Administrative Model]
The Head of School and the Executive Director lead the administrative team at Chesterton Academy of Blessed Michael McGivney. This model of school administration is one of equality with both specific and shared responsibilities.

The Head of School is responsible for internal operations, including the instructional leadership of the school, as well as hiring and supervision of instructional personnel, the curriculum, and student life.

The Executive Director is responsible for the business aspects of the administration including finances, human resources, fundraising, strategic planning, public relations, and building facility.

These co-leaders share responsibilities for nurturing and maintaining the mission and traditions of the school, and ensuring fidelity to the Magisterium.

As a start-up school, we're working towards the model outlined above. We have budgeted for a part-time Executive Director beginning in Year 2, and that role will gradually increase to a full-time Executive Director by Year 4. In the interim, the Board of Directors will fulfill the roles and responsibilities of the Executive Director.

[Summary]
The Head of School serves as the educational leader, responsible for managing the policies, regulations, and procedures to ensure that all students are supervised in a safe, learning environment that adheres to our Catholic identity and meets the approved curricula and mission of the school. The Head of School is responsible for the curriculum, instructional leadership of the school, hiring and supervision of instructional personnel, student life, discipline and related parent communication.

The Head of School must be a practicing Roman Catholic, possess the minimum of a Master's Degree in Education Administration or related field, and demonstrate a commitment to Catholic secondary education. Significant teaching and secondary school administrative experience is required. Salary is competitive and commensurate with experience.

A collaborative relationship between the Head of School and Executive director is a requirement. In addition to any teaching responsibilities, the duties of the Head of School include: (1) curriculum and academic excellence; (2) instruction; (3) student life and discipline; (4) parent communications; (5) student admissions; (6) guidance; (7) other school operations.

[Primary Responsibilities and Duties]

Oversee adherence to Chesterton Schools Network (CSN) curriculum
Oversee implementation of changes to curriculum
Review results of student tests (CLT, PSAT, ACT, SAT)
Oversee school accreditation process and renewal per CSN guidelines

Oversee faculty hiring, evaluation, rehires, terminations
Conduct classroom observations for faculty members as part of evaluation process

Ensure discipline policies are enforced, communicated
Oversee parent-led sports and extracurricular activities
Ensure effectiveness of virtue house and faculty mentor programs
Oversee academic and behavioral eligibility for extra-curricular activities

Send weekly Head of School Missive to parents or school newsletter
Meet with parents regarding student discipline and academic issues

Admit new students upon review of placement exam, student application materials, and meeting
Oversee transfer student process (curriculum, regulations, forms, financial)
Review placement tests and contact parents with remedial needs
Deliver presentations to prospective parents and students at selected school events

Coordinate standardized testing, college applications and transcript preparation
Communicate with colleges, universities and other post-high school programs
Promote various vocational opportunities

Oversee selection and evaluation of vendors (software, textbooks, other services)

[Relationships]
The Head of School maintains the following working relationships:

The Head of School maintains a consultative, collaborative relationship with the Executive Director.
The Head of School maintains a supervisory relationship with faculty and other selected staff, including Administrative Dean and Academic Dean.

[Requirements]

* Education:
Master's in Education Administration or related field

* Experience:
Significant teaching experience in a classical school environment; previous experience in secondary school administration; familiarity with the mission of Chesterton Academy and the teachings of the Catholic Church; and working knowledge of institutional advancement/fundraising.

* Certification:
Not required

* To apply:
Submit your resume, cover letter and three references to chestertonacademybmm@gmail.com.

[About Chesterton Academy of Blessed Michael McGivney]
Chesterton Academy of Blessed Michael McGivney 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. Learn more about Chesterton Academy of Blessed Michael McGivney and the growing national Chesterton Schools Network.

About the Employer

Chesterton Academy of Blessed Michael McGivney is a member of the Chesterton Schools Network (CSN) along with 90+ other schools in the United States and beyond. The CSN is an initiative of the Society of G.K. Chesterton, a lay apostolate canonically established by Archbishop Bernard Hebda in 2018. Under the patronage of G.K. Chesterton & Blessed Michael McGivney our mission is to raise up a new generation of joyful leaders and saints, educated in the classical tradition and the truths of the Catholic faith.