Jan 04, 2024


  • Chesterton Academy of St. Padre Pio
  • Sarasota, FL, USA
Full time Education: Middle/High School

Job Description

Headmaster Position in Sarasota, Florida

Position Details:

As the founding headmaster of Chesterton Academy of St. Padre Pio, this position will have a substantial and immediate impact on the development of our school. Therefore, we are seeking a faithful, joyful disciple of Jesus Christ, who has a passion for classical education. The headmaster should be a prayerful servant leader that is a capable administrator and nurturing educator with an ability to form the character of young people.

As the public face and educational leader of the school, the headmaster will inspire joyful, sacrificial service in students, parents, staff, and our broader community through his or her own Christian example and faithful zeal. The headmaster is responsible for implementing the policies of a rigorous learning environment while adhering to our Catholic teachings and the approved Chesterton Schools Network curriculum. The headmaster will be responsible for hiring and training staff, facilitating fundraising initiatives, and forming a rich, Christ-centered institutional culture.

Administrative Model:

The Headmaster and the Executive Director lead the administrative team. These co-leaders share responsibilities for nurturing and maintaining the mission and vision of the school. Both administrators are hired by and report directly to the Chesterton Academy of St. Padre Pio Board. A collaborative relationship between the Headmaster, the Executive Director, and the Board of Directors is a requirement.

Position Requirements:

• Must be practicing Roman Catholic and demonstrate a commitment to the teachings of the Catholic faith with an Oath of Fidelity to the Church                                                                                   

• Must have a Bachelor's Degree, Master/Doctoral Degree (Preferred)
• Must have experience in secondary school education, 2+ years-experience in educational administration (Preferred)
• 3+ years teaching experience, Classical school teaching experience (Preferred)

Needed Skills:
• Exemplary verbal and written communication skills
• Ability to adapt to various challenges

• Strong interpersonal skills

• Comfortable leading, teaching, and speaking to teens
• A vibrant personal prayer life

• Solid time-management and organizational skills
• Ability to lead small and large groups of people

• Ability to listen and take direction

• Prudent managerial abilities

• Comfortable public speaking

Primary Responsibilities and Duties Include:
Curriculum and Academic Excellence
• Oversee adherence to Chesterton Schools Network curriculum
• Oversee implementation of changes to curriculum
• Oversee annual standardized testing
• Oversee school accreditation process and renewal per Chesterton Schools Network guidelines

• Oversee and participate in fundraising events

• Teach 2 courses initially, subject to change as school grows
• Oversee faculty hiring, evaluation, mentoring, training
• Conduct classroom observations as part of faculty evaluation process

Student Life and Discipline
• Realize the formation of the whole student
• Ensure discipline policies are communicated and enforced
• Oversee parent-led sports and extracurricular activities
• Ensure effectiveness of virtue house and faculty mentor programs
• Oversee academic and behavioral eligibility for extracurricular activities

Parent Communications
• Meet with parents regarding student discipline and academic issues                                                                            • Ignite support and enthusiasm for classical education among faculty, parents and stakeholders
• Leverage position to play a crucial role in recruiting and retaining both students and faculty

• Admit new students upon review of placement exam, student application materials, and interview
• Oversee transfer student process

• Review placement tests and contact parents with remedial needs
• Deliver presentations to prospective parents and students at selected school events

Candidates may familiarize themselves with the Chesterton Academy of St. Padre Pio and Chesterton Schools Network via the links above. Salary is competitive and commensurate with experience.

Please forward a cover letter, resume, and three professional references to board@chestertonsarasota.org.

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