The mission of Trinity Preparatory School of Florida is to develop individuals who will excel in college and in life, contribute to their communities, lead in a changing society, and grow spiritually.

Job Title: Assistant Head of School

Reports to the Head of School

Position Summary: Trinity Preparatory School seeks an Assistant Head of School to lead and assist the school in executing its values to become increasingly attractive, inclusive, and welcoming to a diverse group of faculty and students and what it means to be a Saint. While cultivating relationships throughout the community, this person will be committed to these four core values:

Trinity Family: Our community values traditions, respects the dignity of each member of the Trinity family, and is safe, caring, and supportive.

Educational Excellence, both Academic and Extracurricular: We are committed to encouraging passionate engagement and providing challenging programs, exemplary instruction, and meaningful guidance.

Leadership and Character Development: Our school promotes leadership, ethical behavior, personal responsibility, and reinforces the highest standard of character and honor.

Faith and Spirituality: We affirm the spiritual dimension of life and sustain a community where all are encouraged to explore and deepen their own faith.

Essential Duties And Responsibilities:


Faculty recruitment and onboarding - make recommendations to the head of school and the division directors regarding the hiring, retention, and assignment of faculty.

Identify and deliver metrics and updates on professional and student culture.

Further our formative work (programming) in character development, leadership, diversity and inclusion by:

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.

Talent Development:

People management

Enhance recruiting and hiring strategies to attract employees from diverse backgrounds.

Direct oversight of the fellow and master teacher program.


Align the whole organization and curriculums with character development in mind.

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 guidance to enhance our advisory curriculum.

Assist admissions and advancement to expand our already diverse internal and external community relationships.

Plan and execute the professional development curriculum related to boundaries, bias, and cultural competencies with the Director of Learning and Instruction and Head of School.

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.

Provide ongoing communications regarding focused school-wide activities on community life with the Director of Communications.

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 sted, 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


Excellent verbal and written communication skills including proven dispute resolution skills.

Bachelor’s Degree required; Master’s Degree preferred.

At least 3 to 5 years experience in character development, leadership, and diversity and inclusion 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.


Comprehensive benefits package including medical, dental, vision, life and disability, 403(b) plan

Must be able to pass a Jessica Lunsford Level II background check and drug test.

Trinity Preparatory School is an Equal Opportunity Employer

Job Category:
Management & Professionals
Trinity Preparatory School
Posting Date:
10/29/2021 12:16:52 PM
Winter Park, Florida