Head of School

Naples, FL

Head of School

The Head of School (HOS) is the chief executive responsible for the performance of the school and the primary teacher, advocate, and steward of the schools Mission. A classical school leader/HOS is entrusted with the education and well-being of its students and the academic reputation of that community. The HOS is responsible for training both the mind and heart helping to shape scholars for a life of virtue. The HOS is equally attentive to the school's curriculum, pedagogy, culture, ethical and intellectual living both in and outside of the classroom. The HOS is an example of virtuous living and the love of learning and understands the value of a liberal arts education and can articulate that clearly and effectively. The HOS is a proponent of American classical education informed by the Western tradition, building a culture focused on principled self-government and civic responsibility. 

Qualities and Characteristics:

 •Leadership- The ability to fulfill the nature and purpose of the organization, the ability to inform and inspire people to follow, to commit, to take responsibility, to perform, and to cooperate in an effective manner. The ability to raise up leaders in an organization and build an administrative team that understands and supports the mission. Possess the skill of guiding staff by holding personal integrity, honesty, and decisiveness resulting in trust and confidence with the ability to unify people of diverse backgrounds.

• Intellectual depth and serious understanding of being the leader of an academic institution with a love of learning demonstrated by ongoing personal pursuit of knowledge and the desire to share that knowledge with others. A commitment to school reform with courage and governed by prudence and excellent moral character. The school leader is well-organized and takes responsibility for everything that occurs within the school, carrying out his or her charge with humility and flexibility with a willingness to take on any task even if it seems menial. He or she is keen on delegation with clear direction, yet accountable for every facet of the school.

• A broad understanding of the classical liberal arts, its roots in the Western tradition, and its historical presence in American education. The ability to support teachers in the creation of lessons in collaboration with colleagues and in partnership with the Hillsdale curriculum. The ability to guide, regularly coach and observe teachers in mastering the key elements of their instruction; document results, and provide feedback as mentor and supervisor for the betterment of their students. 

 • The school leader is an advocate for classical education, pleasant, engaging, personable, and empathetic as he or she interacts with parents, community members, teachers, students, and others. The school leader knows how to build trust through excellent communication (in both written and oral forms), which oftentimes means listening, and by being consistent with expectations and follow-through. The school leader is firm, kind, prudent and just. 

The Head of School duties and responsibilities:

  • Maintains a culture that upholds core organizational values: he or she leads according to the tenets of classical education, ensures excellence in teaching and learning, promotes a spirit of community and partnership, and encourages the pursuit of moral and ethical virtue

  • Ensures the school performs in accordance with the law, board policy, school handbooks, and prudence. Maintains all school records and is accountable for school safety

  • Ensures the school meets academic, operational, and financial requirements required by law and the Charter Agreement

  • Ensures the school is compliant with federal requirements for students with disabilities; as well as understands respective state accountability or accreditation system requirements and laws relevant and pertaining to public and private schools

  • Is responsible for leadership, management, and accountability of leadership team members and Administration. Provides general management of all school operations, including academic, financial, personnel, regulatory, and facility areas

  • Holds meetings of school personnel as are necessary for discussion of matters related to the welfare and improvement of the school. Ensures that school patrons and staff are informed of school business 

  • Attends and/or ensures that Administrative staff attends school functions

  • Establishes a culture of academic excellence; is responsible for the selection and performance of instructional coaches and teachers; ensures systems of support to promote constant improvement in teachers’ subject matter and instruction

  • Is responsible for external affairs including but not limited to the public, business and civic organizations, donors and prospective donors, Hillsdale College, authorizers and other government officials and agencies, and accreditors

  • Works with COO to ensure the school operates in accordance with the board-approved budget. Possesses a general understanding of personnel management principles, including recruiting and hiring qualified and competent personnel, supervising, and evaluating individual and organizational development. Reports at regular school board meetings on the status of operations and plans for upcoming activities.  Represents the school as the senior executive leader in interactions with the public, the school constituencies, the authorizer or accreditor, and other government agencies

Required Professional Experience:

  • Required Degree: Masters degree or higher from an accredited college or university.

  • Must have 5+ years of successful Administration experience in a school environment

  • Must have classroom teaching experience and computer literacy skills

  • Must have Hillsdale, classical or comparable curriculum experience

  • School administrator certification preferred 

Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities that are required of the employee for this job. Duties, responsibilities, and activities may change at any time with or without notice.  

The organization is an equal opportunity employer. The organization is committed to providing equal opportunity for all individuals in all areas of recruitment, selection, placement, training, assignment, transfer, compensation, benefits, discipline, retention, and promotion. The board commits itself to the policy that there shall be no unlawful discrimination against any person because of race, color, religion, age, sex, national origin or disability. All decisions with regard to employment shall be in compliance with applicable state and federal laws.