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Careers at The Chesterton Schools Network
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Head of School

22 Oct 2025
New Haven, CT, USA
Verified by Turrior

Content + Source + Freshness • 12 Dec 2025 • 95% confidence

80 / 100

Offer value

The Head of School role presents a unique opportunity to influence a new educational initiative, though candidates may face challenges related to startup dynamics and undefined salary.

  • Play a critical role in establishing a new school
  • Competitive responsibilities with potential community impact
  • Engagement in all administrative functions
  • Salary information is not defined, which could limit interest
Pros
  • Foundational role in establishing a new academic culture
  • Involvement in all aspects of school administration
  • Potential for significant community engagement
Cons
  • Startup challenges can create instability
  • Undefined salary parameters may deter experienced candidates
  • High level of responsibility can impact work-life balance

Who it's for

Senior / Executive • On-site

Good fit
  • Experienced educational leaders
  • Innovators passionate about Catholic values
  • Talented individuals eager to impact student lives
Not recommended for
  • Candidates without educational management experience
  • Individuals resistant to community involvement
  • Those seeking predefined roles in established schools

Motivation fit

Eagerness to lead and innovate in educational settingsDesire to foster a strong school cultureCommitment to promoting Catholic values in education

Key skills

Educational administrationLeadership and managementCurriculum developmentCommunity relations
Score: 80/100 AI verified analysis

About the job

Job Description

SUMMARY
The Head of School of Chesterton Academy of Blessed Michael McGivney 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 & DUTIES
1) Curriculum and Academic Excellence
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

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

3) Student Life and Discipline
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

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

5) Admissions
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

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

7) Other School Operations
Oversee selection and evaluation of vendors (software, textbooks, other services)

8) Teaching Responsibilities (as needed)

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.

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.

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

Chesterton Academy of Blessed Michael McGivney complies with all federal and state employment laws and regulations. Applicants must be lawfully authorized to work for any employer in the United States. We are unable to sponsor or take over sponsorship of an employment visa for this position. Applicants must be legal residents of the United States and possess a green card if not a US citizen. Moving expenses will not be reimbursed. This is not a remote position and reliable transportation is required.

TO APPLY
Submit your resume, cover letter and three references to chestertonacademybmm@gmail.com

About the Employer

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. Under the patronage of G.K. Chesterton & Blessed Michael McGivney our mission is to raise up a new generation of joyful leaders and saints.

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