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Dean of Students

Naples Classical Academy
Naples, FL Full Time
POSTED ON 5/5/2026
AVAILABLE BEFORE 6/3/2026
Now Hiring!

Naples Classical Academy seeks a full-time Dean of Students (DOS) to join our team. The Dean of Students oversees discipline with compassion fostering an engaging and supportive environment for all students. The Dean will play a vital role in ensuring student success, wellbeing, and development by working collaboratively with faculty, staff, students, and families. The DOS will interact and build relationships with all students and teachers, providing mentorship and oversight. The Dean will serve as advocate for students and families, addressing concerns, communicating and working to resolve issues in a timely manner. The Dean provides leadership and oversight for programs and services that enhance and engage students, creating a culture in which collaboration and collegiality guide relationships and decision making.

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.

The responsibilities of this role include, but are not limited to, the following:

  • Support and promote the school’s mission and the principles of classical education.
  • Act in a virtuous and professional manner
  • Maintain a safe and respectful learning environment
  • Coordinate with operations to manage school safety within federal/state law and the emergency management plan.
  • Hold and maintain high standards of student conduct; communicate and enforce the Code of Student Conduct firmly, fairly, and consistently in total compliance with due process procedures.
  • Design and carry out a comprehensive student activities program to recognize student achievement and create opportunities for student participation.
  • Make arrangements for conferences when needed.
  • Manages school discipline, treating students with respect and fairness while enforcing the NCA Family Handbook policies for attendance, uniform and behavior.
  • Communicates well with students and parents to develop relationships, and a trusting rapport.
  • Is committed to mentorship and just discipline, in terms of developing student character and sustaining the schools moral identity.
  • Collect and analyze student performance data to identify curricular gaps and improve instruction and recommend needed changes to support student life.
  • Participates in training, professional development and assists in onboarding new staff
  • Model excellent classroom management, content expertise, and classical pedagogy.
  • Support fellow Administrators in operations and daily activities.
  • Speaks comfortably and collaboratively with parents
  • Assists with managing testing (training, schedule, setup and data reflection.)
  • Supports HOS by helping with operational items as needed and assigned in managing school safety, discipline, and special programs.
  • Uses due process, proper documentation and communicates consequences with the students and parents in a way that can help instill virtue in our students while protecting the learning environment.
  • Establishes a master schedule to ensure compliance with instructional time and prepares and oversees the preparation of reports, lists and other documentation as needed for compliance, scheduling and efficiency.
  • Establish and maintain an effective learning climate and maintain active relationships with students and parents/guardians.
  • Any and all duties as assigned by the HOS

Qualified Candidates Will Meet The Following Requirements

  • A Bachelor's Degree from a fully accredited college is required.
  • Valid teaching certification is preferred.
  • Previous experience in classical education is preferred.
  • Leadership experience in a wide range of grade levels from elementary school through high school.
  • Candidates should possess excellent written and oral communication skills.
  • At least 2 years of experience in school Administration and at least 3 years in a K-12 school educational environment
  • The ability to use technology effectively

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 law

Salary.com Estimation for Dean of Students in Naples, FL
$98,358 to $130,654
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