Assistant Head of Middle School - Students

Community School of Naples (CSN) is seeking a strategic and dynamic Assistant Head of Middle School-Students. Assistant Head of Middle School-Students is a member of the Middle School Leadership Team and, as such, is responsible for the development of school policies related to the student life on campus, implementation of the CSN mission, and creation of a safe and supportive environment necessary to achieve success. Assistant Head of Middle School-Students shares with the Head of Middle School the responsibility for protecting the health and welfare of students and, to that end, maintains a visible daily presence on campus both during the course of the day and in the evenings as necessary. The role keeps the Head fully informed on student issues and all other relevant matters pertaining to school life.

Community School of Naples is one of the top independent schools in southwest Florida and maintains a Pre-K3-12 school enrollment of approximately 1000 students. CSN has a high retention rate with many dedicated teachers here for longer than 10 years; some more than 30. CSN students track higher than all other southwest Florida schools in test scores, extracurricular activities, and college acceptances. The school’s beautiful 77-acre campus features lush landscaping, many ponds, and an open atmosphere.

Job responsibilities include:

• Serve as a positive, energetic, and effective member of the Middle School Leadership Team (MSLT).

• Enforce all regulations of the School Handbook.
• Provide student supervision throughout the day, during lunchtime and while travelling around the campus.
• Manage student discipline, ensuring fair and consistent application of school policies and procedures in a compassionate and comprehensive manner; be assertive or growth-oriented as needed.
• Communicate with parents, students and faculty to keep students accountable for unacceptable behaviors.
• Respond to student concerns and inquiries, providing guidance and support to navigate school challenges.
• Oversee all matters of student attendance, including investigating attendance problems, assigning students appropriate consequences for tardiness, class cuts and truancy, and publishing a daily log of student absences for faculty.
• Oversee policies related to students and support the faculty by developing classroom management programs.
• Develop and lead proactive programs to improve student behaviors, culture, and interactions.
• Promote a positive environment by fostering respect, responsibility and trust among colleagues and students.
• Ensure that all decisions are in alignment with the CSN’s mission and further the school’s goals and advancement.
• Oversee and create lessons for the Middle School advisory program.
• Create and deliver weekly presentations at Middle School assemblies, seek opportunities to bring guest speakers/programs to the Middle School that align with CSN’s core values.
• Collaborate with the Assistant Head of Academics to create daily schedules for special event days (standardized testing, guest speakers, midterms/finals, etc.).
• Contribute to hiring processes.
• Teach the equivalent of one everyday class from August to May.
• Other responsibilities as assigned by the Head of Middle School.

Requirements:

• A Bachelor’s degree, although Master’s preferred, in Educational Leadership or related field of study.
• A minimum of two years in school administration or related leadership experience.
• A minimum of three years teaching experience at the middle school level.
• Prior independent school experience is preferred.
• Possess highly effective communication and interpersonal skills to handle conversations with students, parents, and colleagues with tact, diplomacy and grace.
• Proven track record of success in demonstrating a positive, solution-oriented temperament.
• Must be able to work in a fast-paced environment aiming at meeting multiple competing tasks and demands; ability to stay calm under pressure.

Compensation and Benefits:

The appointment will be for the academic year of August 2025 through August 2026. This is a full-time administrative position paid on an annual salary commensurate with experience, degree attainment and other qualifications. This position is eligible for CSN’s competitive benefit package, which includes medical, dental, vision, short- & long-term disability, life insurance, 403(b) retirement program with a generous match, Aflac, and Legal Shield offerings. Additional benefits include generous time-off (academic recesses and summer) and the use of the school’s state-of-the-art recreational facilities. Complimentary breakfast and lunch are served on all school days. Please visit our website for more details about the benefits of a career at CSN.

• Community School of Naples is an Equal Opportunity Employer.
• Fingerprinting and background checks are a required part of CSN’s employment eligibility process.