Assistant Head of School

Available Position: Assistant Head of School

Department: Administration/Wellness

Reports to: Head of School

Full/Part-time: Full-time

Date Posted: February 10, 2026

Start Date: July 1, 2026

Trinity Preparatory School is an independent, coeducational college‑preparatory school that develops ethical, resilient leaders who thrive in the pursuit of excellence, embrace diversity in thought and perspective, and grow spiritually. In alignment with our mission, we affirm our commitment to our four core values:
Trinity Family;
Educational Excellence, both Academic and Extracurricular;
Leadership and Character Development; and Faith and Spirituality. In 1968, a dedicated group of Orlando community leaders led by the late Reverend Canon

A. Rees Hay wanted to provide a quality, independent secondary education for students in Central Florida. As a result, they established Trinity Preparatory School in grades 6 through 12. Affiliated with the Episcopal Church, the school welcomes families and students from all faith traditions, cultures, and backgrounds. Our devoted and notable faculty and staff are leaders in their field who share their knowledge and expertise with others at various professional development opportunities worldwide.

Their dedication is demonstrated to our students, families, and communities both in and out of the classroom with a balance of academic rigor and wellness. Trinity’s student body and families reflect the world as they travel from the greater Orlando area and across the nation to take part in the Trinity experience.

Trinity Preparatory School of Florida seeks an Assistant Head of School who will report and work closely with the Head of School and serve as a member of the senior administrative team to care for all students in a fast‑paced learning environment. The ideal candidate possesses highly developed interpersonal skill; thinks critically throughout the decision‑making process; and is a creative problem solver.

This role leads and assists the school in executing its values to become increasingly attractive and welcoming to a diverse faculty, staff, and students in what it means to be a Saint. Through strategic planning, facilitating and evaluating, this role ensures alignment with mission‑driven outcomes.

• Demonstrates Self‑Awareness
• Ensures Accountability
• Communicates Effectively
• Cultivates Innovation

• Strategic Mindset
• Values Differences
• Manages Complexities
• Drives Vision and Purpose

Leadership:

• Faculty recruitment and onboarding - make recommendations to the head of school and the division directors regarding the hiring, retention, and assignment of faculty.
• Enhance recruiting and hiring strategies to attract employees from various backgrounds.
• Direct oversight of the fellow and master teacher program.
• Align entire professional culture in accordance with Four Core values.
• Identify and deliver metrics and updates on professional and student culture.
• Further our formative work in character development.
• Strengthening our current relationship with the Boys and Girls Club of Central Florida and other community groups.
• Generate regular and ongoing professional development opportunities for employees.
• Provide educational opportunities to students, parents, and alumni with regard to all areas of community wellness.

Wellness:

• Oversee the work of the wellness department with supervisory responsibilities over the school counselors, learning support staff, administrative assistant, and nurse.
• Work with the wellness team to develop, implement, and evaluate comprehensive programs to support the physical, intellectual, social, and emotional health of our students.
• Identify and coordinate outside professional development for faculty and staff.
• Oversee and facilitate faculty in‑service schedules.

In collaboration with faculty and other school leaders, the Assistant Head of School will:

• Assist our division heads and school chaplain to establish and execute a character development program.
• Assist the school chaplain with establishing an all‑school servant…