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Teaching at Trinity Prep is profoundly satisfying, especially because of the students.
I've never been around a group of young people as smart, enthusiastic, and spirited
as I have found here."
Robert Boerth, English teacher

About Trinity Prep

Trinity Preparatory School is an independent, coeducational, college preparatory school serving more than 860 students in grades six through 12. We are affiliated with the Episcopal Church, and our 100-acre campus in Winter Park, Florida is surrounded by two beautiful lakes.

Our staff and faculty embody a tradition of high performance, growth, development, and professional demeanor. Salaries and benefits are competitive with top national peer schools. Class sizes are small, and our state-of-the-art facilities ignite learning and passion. In addition, the school pays into a retirement program and offers tuition remission for faculty and staff who qualify. If you are are interested in joining our Trinity family, check out the following employment opportunities.

Positions are posted as the need for new coaches, faculty and staff arises. Trinity Preparatory School does not discriminate on the basis of race, color, religion, sex, or national/ethnic origin in employment, educational policies, admissions policies, scholarship athletics, or other school-administered programs.

Faculty / Staff Positions

Qualified Substitute Teachers

Director of Advancement

Trinity Preparatory School, a premier private school of nearly 900 students grade 6-12 grade in Winter Park, Florida, is seeking an experienced fundraiser, engaged leader and committed communicator to serve as its next Executive Director of Advancement. The successful candidate will share and promote the core values embodied by Trinity Prep, its faculty, staff, students, parents and alumni in its mission to develop individuals who will excel in college and in life, contribute to their communities, lead in a changing society and grow spiritually. The right candidate will help build a culture of giving at Trinity Prep, with supreme emphasis on gifts to the Trinity Prep Fund, through creative leadership, the ability to ask and problem solving.

The new Director of Advancement will:

  • Be a leader for the entire Trinity family, communicating and engendering passion for the mission of the School and guiding excellence in every aspect of the Advancement division.
  • The Executive Director will foster active partnerships, develop productive relationships and be fully vested in the Trinity and greater Orlando communities.
  • As the chief external relations officer for the School, the Executive Director will have strict monthly visit goals for themselves, and the Advancement Team, to actively engage constituents in supporting Trinity Prep.
  • Provide support for the Head of School in strategic thinking and planning for Trinity Prep and for fundraising work, cultivating the valuable relationships that will increase support for Trinity.
  • The Executive Director will support the Board of Trustees, especially the Governance and Development Committees.
  • Collaborate with the senior leaders, known as the “A-Team” to address School-wide challenges and create funding plans to achieve institutional objectives.
  • Foster a sense of urgency about the work of the Advancement team (especially the Trinity Prep Fund, but also major gifts and planned giving, and alumni and parent engagement and communications) and its potential to contribute to the future of the School.
  • The Executive Director will lead long-range planning for the Advancement division ensuring that stretch goals are set and achieved to support the School’s strategic plan initiatives and annual giving goals.
  • As the new strategic plan is unfolding and major gifts and planned giving programs are being developed, significant emphasis will be placed on growing a robust Trinity Prep Fund to include active face-to-face solicitations, superior direct marketing and phone-a- thon programs and growing an active network of volunteer fundraisers.
  • Grow and lead a staff committed to developing and enacting best practices with regard to donor discovery, cultivation and stewardship, communications, metrics and staff accountability, and professional development.
  • Create a comprehensive parent program, characterized by more robust parent engagement and financial support for the short and long-term benefit of Trinity Prep.
  • Enhance alumni engagement by developing comprehensive plans of communication, activities and programs to enlist all alumni, young and older, as volunteers, advocates and donors of the School.
  • Manage a personal portfolio of donors (including Trustees, major and planned gifts and high-end annual giving prospects) and meet individual goals for visits.

Specific Qualifications

  • Candidates with 5−10 years of increasing responsibility in the advancement field are encouraged to apply.
  • Previous experience at premier independent schools with compatible missions required.

Other qualifications include:

  • Bachelor’s degree required; advanced degree preferred.
  • Demonstrated knowledge of major gifts work, planned giving and leading a successful annual giving program a must.
  • Successful capital campaign experience.
  • Excellent planning and creative strategic thinking skills.
  • Strong leadership and motivational ability.
  • Excellent communication skills, both verbal and written.
  • Strong management skills and the ability to attract new talent.
  • Strong results-oriented focus driven by well-established metrics and accountability.
  • Team player with ability to collaborate with dynamic leadership team at the executive level.

Apply Now


Summary Maintains and repairs physical structures of buildings and maintains grounds by performing the following duties.

Essential Duties and Responsibilities include the following. Other duties may be assigned.

Receives written work orders or verbal instructions from supervisor.

Cuts grass and trims weeds on school's property.

Paints interior and exterior walls and trim.

Maintains and repairs buildings' plumbing, electrical systems and air conditioning systems, including replacing worn or defective parts such as switches and fuses.

Maintains and repairs wood parts of buildings.

Assists other departments with moving furniture and unloading and storing supplies.

Qualifications To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed below are representative of the knowledge, skill, and/or ability required. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

Education and/or Experience

High school diploma or general education degree (GED); or one to three months related experience and/or training; or equivalent combination of education and experience.

Reasoning Ability

Ability to apply common sense understanding to carry out detailed but uninvolved written or oral instructions. Ability to deal with problems involving a few concrete variables in standardized situations.

Other Qualifications

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

Must be able to pass a drug test.

Physical Demands The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

While performing the duties of this Job, the employee is regularly required to stand; walk; use hands to finger, handle, or feel; reach with hands and arms; climb or balance; stoop, kneel, crouch, or crawl and talk or hear. The employee is occasionally required to sit. The employee must regularly lift and /or move a minimum of 50 pounds.

Work Environment The work environment characteristics described here are representative of those an employee encounters while performing the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

While performing the duties of this Job, the employee is regularly exposed to moving mechanical parts; high, precarious places; fumes or airborne particles; toxic or caustic chemicals and outside weather conditions. The noise level in the work environment is usually moderate to loud.

Apply Now


Position: Videographer

Responsibilities are listed, but are not limited to:

  • Creating visual and tonal consistency throughout all creative products
  • Gather and propose ideas for new video; utilize video script writing fundamentals and set a production schedule prior to shoot
  • Performing all visual storytelling for the school, including admission, development, and alumni materials, arts publications, and more
  • Coordinating social media posts with video and other motion graphics as necessary
  • Managing occasional content and design changes to the website
  • Conceptualizing, shooting, and editing short videos for various applications
  • Collecting and managing/organizing all digital assets
  • Other duties as needed by the manager of marketing and communications
  • May teach a course in short film making, graphic design,
  • May perform some graphic design work


  • Bachelor’s degree or pursuit of a degree in videography and/or photography
  • Understanding of brand management, marketing and communications strategies, and skill in translating messages into integrated marketing campaigns
  • Intermediate to advanced video and editing capabilities
  • Exceptional interpersonal skills and the ability to meet deadlines
  • Knowledge on how to engage audiences using social media: YouTube, Twitter, Facebook and Instagram
  • Proficiency using some or all of the Adobe Creative Suite/Cloud; Premiere, After Effects, Final Cut Pro or similar

Additional Qualifications:

  • Understanding of HTML, CSS, and Javascript is a plus
  • Experience in the education sector is a plus
  • Experience using aerial photography equipment is a plus

Apply Now

Coaching Positions

Candidates must be at least 21 years old and available from 3 to 7 p.m. during the season.

If you have any questions regarding employment opportunities, please send an email to All applicants must be able to pass a level II Jessica Lunsford background check and drug test.

Employee Nondiscrimination Policy

We are committed to providing equal opportunity in all of our employment practices, including selection, hiring, promotion, transfer, and compensation, to all qualified applicants and employees without regard to age, race, color, sex, national origin, citizenship status, marital status, religion, disability/handicap, sexual orientation/gender expression, or any other protected status in accordance with the requirements of all federal, state, and local laws. If you believe you have been treated inconsistently with this policy, please immediately report your concern to a member of the Administrative Council or Human Resources. You will not be retaliated against for bringing forth a complaint in good faith.