Headmaster/Headmistress

Summary
The Headmaster 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 Headmaster is responsible for the
curriculum, instructional leadership of the school, hiring and supervision of
instructional personnel, student life, discipline and related parent communication.
The Headmaster must be a practicing Roman Catholic, possess the minimum of a
Master’s Degree in Education Administration or related field or equivalent
experience, and demonstrate a commitment to Catholic secondary education.
Salary is competitive and commensurate with experience.
The Board of Directors appoints the Headmaster of Chesterton Academy. In addition
to any teaching responsibilities, the duties of the Headmaster 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
Curriculum and Academic Excellence
• Oversee implementation of and adherence to Chesterton Schools Network
curriculum
• Oversee implementation of any changes to the curriculum
• Review results of student tests (CLT, PSAT, ACT, SAT)
• Oversee school accreditation process and renewal per Network guidelines
Instruction
• Oversee faculty hiring, evaluation, rehires and terminations
• Conduct classroom observations for faculty members as part of the
evaluation process
Student Life and Discipline
• Ensure discipline policies are enforced and 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
Parent Communications
• Send weekly Headmaster Missive to parents or include in school
newsletter
• Meet with parents regarding student discipline and academic issues
Admissions
• Admit new students upon review of placement exam, student application
materials, and meeting
• Oversee transfer student process (curriculum, regulations, forms,
financials)
• Review placement tests and contact parents concerning any student
remediation
• Deliver presentations to prospective parents and students at selected
school events
Guidance
• Coordinate standardized testing, college applications and transcript
preparation
• Communicate with colleges, universities and other post-high school
programs
• Promote various vocational opportunities
Other School Operations
• Oversee selection and evaluation of vendor products (software, textbooks,
etc.)
Teaching Responsibilities
• Fill in as needed
Working Relationships
The Headmaster maintains the following working relationships:
• The Headmaster reports directly to the Board of Directors.
• The Headmaster maintains a supervisory relationship with faculty and
other selected staff.
Requirements
Education:
Masters in Education Administration or related field or equivalent experience
Experience:
Significant teaching experience in a classical school environment Is preferred;
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
About Chesterton Academy
Founded in 2008 as a result of a grass-roots movement of parents, Chesterton
Academy 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 and the growing national Chesterton