Now Hiring for SY 26/27

Dean of Upper School 

The Dean of upper school is a 12 month full time in person position that reports directly to the Head of School (HOS) and serves as a key academic and cultural leader within the school. This role is primarily responsible for the formation, mentorship, and evaluation of faculty, ensuring fidelity to the classical model of education and the intellectual and moral mission of a Hillsdale-affiliated charter school. The Dean supports excellence in instruction, the cultivation of virtue, and the professional growth of teachers through consistent coaching, observation, and development. Additionally, the Dean will partner with the Head of School and administrative team to support the intellectual, moral, and behavioral formation of students in alignment with the school’s mission. Promote a culture of virtue, responsibility, and respect by upholding and consistently enforcing school-wide expectations for student conduct. Collaborate with administration to address student discipline matters with clarity, consistency, and a commitment to restorative and formative practices. Support and, when appropriate, directly engage in student mentorship, guiding students in habits of character, academic responsibility, and civic virtue. Work closely with faculty to ensure classroom management practices reflect the principles of classical education and contribute to a coherent school culture. Communicate with students and families regarding behavioral expectations and disciplinary outcomes in a manner that is respectful, clear, and mission-aligned.

Strong candidates will support the school’s Mission: to develop students in mind and character through a classical, content-rich curriculum that emphasizes the principles of virtuous living, traditional learning, and civic responsibility. They will have enthusiasm for the vision and mission of NCA.

About Naples Classical Academy:

A Tuition-Free Public Charter Classical School. Naples Classical Academy is a Hillsdale College Member School.

NCA's mission is to train the minds and improve the hearts of students through a classical, content-rich curriculum that emphasizes virtuous living, traditional learning, and civic responsibility.

Requirements

The ideal candidate will:

• Demonstrate a deep commitment to the principles of classical education and the mission of Hillsdale-affiliated schools

• Embody and actively promote the school’s core virtues, fostering a culture of intellectual and moral formation

• Exhibit exceptional attention to detail and a commitment to excellence in all aspects of academic life

• Diagnose instructional or programmatic challenges, research effective solutions, and lead faculty in their implementation

• Be devoted to mentorship and the cultivation of future instructional and institutional leaders

• Communicate clearly, respectfully, and collaboratively with parents, faculty, and school leadership

• Approach difficult conversations with clarity, courage, and a steadfast commitment to the school’s mission

Primary Responsibilities

Program Fidelity & Curriculum Stewardship

• Safeguard fidelity to the Hillsdale K–12 Program Guide, ensuring coherence and continuity across grade levels and disciplines

• Promote the ordered development of knowledge, emphasizing the liberal arts tradition and the pursuit of truth, goodness, and beauty

• Provide informed recommendations to the HOS regarding curricular refinement or improvement

• Develop and implement systems to assess alignment with the Hillsdale curriculum and instructional expectations

Faculty Formation & Mentorship

• In partnership with the HOS, establish annual professional development priorities aligned with the school’s academic vision and allocate professional development resources accordingly

• Lead and implement a structured induction program for new faculty, grounded in classical pedagogy and school culture

• Guide faculty in setting and pursuing individualized professional goals rooted in the school’s instructional framework and the principles of classical education

• Conduct regular classroom observations and evaluations, providing substantive, actionable feedback, with particular attention to the development of new teachers

• Cultivate a faculty culture marked by a love of learning, intellectual seriousness, and the joyful pursuit of excellence in teaching

• Encourage the deepening of teachers’ content knowledge and their mastery of classical pedagogical practices

Administrative Leadership & Support

• Advise the HOS on faculty evaluations and professional growth trajectories

• Collaborate with the Administration team in planning and leading faculty meetings that reinforce the school’s mission and instructional priorities

• Oversee and communicate the academic calendar, including assessments and events that affect instructional time (e.g., assemblies, drills)

• Coordinate and schedule parent-teacher conferences in a manner that supports strong school-family partnerships 

• Read and comply with the Employee Handbook and NCA policies

• Perform all other duties as assigned.

Qualified candidates will meet the following requirements:

● A Bachelor's Degree in Education or related field (from a fully accredited college) is required (Master’s degree preferred).

● Valid Florida teaching certification is preferred.

● Previous experience in classical education is required (Hillsdale preferred).

● Leadership experience in a wide range of grade levels from elementary

school through high school. 

● Candidates should possess excellent written and oral skills as well as basic technology skills.

● At least 3 years of experience in school Administration. 

● Minimum of 5 years of classroom experience, with demonstrated excellence in instruction.