Posted: 10-Feb-26
Location: Winter Park, Florida
Type: Full Time
Preferred Education:
About the Trinity Preparatory School of Florida:
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.
Position Summary:
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 fact-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.
The Assistant Head of 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 Assistant Head of School will exemplify Trinity Prep’s Leadership Competencies:
- Strategic Mindset
- Values Differences
- Manages Complexities
- Drives Vision and Purpose
Essential Duties And Responsibilities:
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 (programming) 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 leadership curriculum inclusive of our Episcopal identity.
- Assist school counselors to enhance our advisory curriculum.
- Assist admissions and advancement to enhance and expand internal and external community relationships.
- Plan and execute the professional development curriculum related to boundaries, bias, and cultural competencies with the Head of School and other school administrators.
- Perform risk management with Human Resources. Maintains knowledge of diversity-related issues, legislation, and best practices. Provides training and policy updates to colleagues, ensuring legal compliance of management and human resources staff.
Additional Expectations:
- Consult and advise the Head of School
- Special project or program inception, development, and execution
- Present to the Board of Trustees/employees as required or requested
- Serve in the head of school’s stead where and when appropriate
- Sit on the Curriculum Committee or committees as assigned by the Head of School
- Teach or coach as appropriate
- Attend conferences and training as required to accomplish project goals
Qualifications and Experience:
- Excellent verbal and written communication skills including proven dispute resolution skills.
- Minimum of a bachelor’s degree from an accredited institution or the international equivalent with a focus on related fields; Master’s Degree preferred.
- At least 3 to 5 years experience in character development, leadership, and wellness programming required.
- Episcopal Priests are encouraged to apply.
- Excellent organizational skills and attention to detail.
- Strong analytical and problem-solving skills.
- Proficient with G Suite or related software.
Certifications Required:
- CPR/AED/First Aid are able to be gained upon hiring.
Benefits:
- Comprehensive benefits package including medical, dental, vision, life and disability, 403(b) plan
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.
Employee Nondiscrimination Policy:
- Trinity Preparatory School is an Equal Opportunity Employer.
Application Requirements:
- Interested candidates should complete an application through the below link: APPLY NOW
- This position will remain open until filled.