Head of Middle School 2025-2026

Position Summary: The Head of Middle School is responsible for all duties attending the planning and supervision of daily life for a diverse middle school (grades 6-8), its dedicated faculty, and for maintaining an education of the highest standard. The Head of Middle School reports to the Head of School, and assumes general responsibility for the conduct and welfare of students in those grades. He/she collaborates with the Head of School, Associate Head of School and the Department Heads to lead research-based, innovative learning and teaching, and ensure that school policies are pursued in this division. This educational leader will assist in recruiting, admitting, onboarding, retaining, managing, supporting, and separating faculty, staff, students, and parents. This position will remain open until filled. Strategic Leadership Initiative: Champion the mission while maximizing human performance. Learning Atmosphere and Professional Culture: Trinity Prep has a one-to-one laptop program, and students use technology in a variety of ways in every discipline. For example, students integrate electronic textbooks, utilize Google Docs and Forms for assignments, and apply blended models to ignite teacher-student interaction. Using our learning management system, Canvas, and participating in the advisory program are required professional standards. The Head of Middle School will exemplify Trinity Prep’s four Core Leadership Competencies that apply to all employees of the organization: Demonstrates Self-Awareness Ensures Accountability Communicates Effectively Cultivates Innovation In addition, the Head of Middle School will exemplify Trinity Prep’s four Leadership Competencies that apply to all divisional leaders of the organization: Optimizes Work Processes Drives Vision and Purpose Customer Focused Decision Quality Self-Development and Learning Duties and Responsibilities: Report to the Head of School. Maintain academic excellence with a unique and dynamic environment that actively promotes multiple cultures, religions, and languages in an Episcopal school. Assist in recruiting, onboarding, retaining, managing, and supporting faculty and staff; students and parents. Communicate the goals and philosophy of the middle school. Consult with parents when necessary with regard to or on behalf of students and/or teachers. Supervise middle school extra-curricular activities and the scheduling of middle school events with advisors, counsel students on academics, co-curricular choices, and social activities. Refer students to the Learning Specialist and Middle School Guidance Counselor for testing and/or counseling appropriately. Support the Chaplain in the administration of middle school community service efforts. Lead and oversee middle school assemblies and programs. Monitor student behavior and ensure the enforcement of the discipline system. Teach a class and serve as an adviser. Assist in the hiring, assignment of responsibilities, and evaluation of professionals for retention and advancement. Oversight responsibilities include: Dean’s Office (discipline) Administrative support personnel Student Activities Coordinator and Class Sponsors Middle School budget Committee responsibilities: Administrative Team Admission Committee Curriculum Committee Liaison with Trinity Parents’ Association grade-level representatives Perform duties as assigned by the Head of School. Qualifications and Experience: Preferred experience in urban setting or full-time boarding school. Outstanding written and oral communication skills. Proven experience making independent judgments and handling highly confidential and sensitive materials and situations in ways that respect the dignity of each individual. The ability to navigate a wide range of relationships, tasks and perspectives; working with independent school faculty and staff preferred. Mastery in teaching, curriculum development and instructional design, academic technologies, and modern teaching practices. Experience developing and leading programs. Demonstrated leadership experience, including the ability to manage direct reports and co-lead with other administrators. An affinity for details; exceptional organizational and time-management skills; and demonstrated strength with analysis and problem-solving. Evidence of a strong work ethic, a high level of integrity, and energy and enthusiasm about working with primary school through eighth grade faculty in an academic setting. A successful track record of collaboration and experience supporting a wide range of constituents. Bachelor’s degree required; master’s degree or additional certifications preferred. Certifications Required: CPR/AED/First Aid can be obtained upon hiring. Benefits: Comprehensive benefits package including medical, dental, vision, life and disability, 403(b) plans. Safeguarding for Children and Youth: Trinity Preparatory School of Florida is committed to ensuring the safeguarding and well-being of its students and expects all faculty, staff, and volunteers to share this commitment. The recruitment process at TPSF is carried out in accordance with recommendations of the Episcopal Diocese of Central Florida on Protection for Children and Youth from Abuse and includes rigorous background checks prior to appointment and additional training after appointment. Application Requirements: Interested candidates should complete an application through the below link: APPLY NOW

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