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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

English Teacher

Trinity Preparatory School, a coeducational school for 875 students in grades 6 through 12 in Winter Park, FL, seeks a dynamic and enthusiastic full-time English instructor to teach five sections of English at the middle and/or upper school levels. Candidates must have the desire and ability to work with students who are highly motivated to learn and achieve and colleagues who are passionate about their craft. This teacher should plan to be an integral component of the students' lives, in and out of the classroom, and to collaborate with colleagues on a grade-level team and as a member of the English Department.

Qualified candidates will have a bachelor’s degree in English or higher and demonstrate broad content knowledge across a variety of literary genres. Trinity Prep has a one-to-one laptop program, and students use technology in a variety of ways in every discipline. Using our learning management system Canvas and participating in the advisory program are required professional standards. In addition to teaching and advising, Trinity faculty lead a significant out-of-the-classroom activity like coaching a sport or a competitive academic team.

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Part Time Security

Trinity Preparatory School is currently seeking a part-time security guard to work flexible hours. Security at Trinity Preparatory is 24/7 so the hours could be daytime, third shift or weekends. Candidates must be licensed as a class D security officer and be able to work any shift. Position requires patrolling the property, monitoring surveillance equipment, inspecting buildings, equipment and access points, controlling traffic and completing reports. Trinity is a non-smoking environment. Must be able to pass a level II background check and drug test. All interested applicants should complete an application by selecting apply for a Faculty/Staff position above.


School Chaplain

Trinity Preparatory School, an independent, coeducational college preparatory school serving more than 860 students in grades six through 12, seeks an ordained Episcopal priest; a thoughtful intellectual who can inspire and lead our community as chaplain for the 2017-2018 school year.

The chaplain reports to the Head of School and maintains a highly public role at Trinity Prep and in the cities of Orlando and Winter Park, Florida. His/her primary responsibility is to care for the overall spiritual life of the school and maintain our identity as an Episcopal School. The Chaplain is solidly grounded in the Christian faith, yet comfortable working in a religiously diverse community. The Chaplain’s responsibilities include conducting weekly Chapel services for upper and middle school divisions, providing pastoral counseling, supervising religious clubs, supervising Bible studies, and organizing the major liturgical events which fall within the school year. In addition, he/she teaches elective courses in religious studies and ethics, organizes and coordinates the school’s community service program (with assistance), and actively participates in the extracurricular life of the school through coaching and attending student events as appropriate.


  • Plan, organize, and lead weekly, divisional chapel services (currently one service for each division) that are developmentally appropriate and reflect the mission and values of the school through Bible readings, liturgy, song, and other spiritual messages
  • Coordinate with the chapel music directors
  • Model and encourage regular prayer
  • Plan, organize, and lead school Eucharist services
  • Recruit guest chapel speakers
  • Recruit students to fill leadership roles in all chapel services
  • Maintain all worship “equipment” and supplies
  • Establish a chapel curriculum and deliver heartfelt, inspiring homilies


  • Provide pastoral counseling services to students and their families, faculty, staff, and the larger Trinity community as needed
  • Assist in the coordination of parent-led support systems for community members in times of crisis
  • Be involved in all leadership and character development discussions, program creation and management
  • Lead the school’s response to bereavement

Teaching and Coaching:

  • Teach religion and ethics classes as assigned
  • Perform coaching duties as appropriate


  • Represent the school in such a way that reflects the mission, core values, and Episcopal identity of Trinity Prep

Service Learning:

  • Create service learning models that encourage students to develop a service-oriented mindset while also being sensitive to the specific needs of the populations served
  • Provide leadership in the Habitat for Humanity project


  • Serve as a member of the leadership team and attend meetings as planned
  • Prepare chaplain’s annual budget and operate under the guidelines of that budget
  • Attend faculty and staff meetings as necessary
  • Participate in student supervision duties
  • Participate in diocesan affairs as desired or as required, and serve as a liaison with the Bishop
  • Present periodically to the Board of Trustees


  • Maintain a personal life in accordance with Safeguarding God’s Children and Safeguarding God’s People
  • Be committed to the principles of the Episcopal Identity of the school as determined by our membership in the National Association of Episcopal Schools and the Central Florida Episcopal Schools Association.
  • Display outstanding organizational and communication skills, fair judgment, and keen problem solving
  • Meet regularly with and perform duties as assigned by the Head of School

Interested candidates should complete an application through the link above: Apply for a Faculty/ Staff Position


Trinity Preparatory School is seeking an enthusiastic recent college graduate interested in pursuing a career in education to participate in our Fellowship Program. The individual will serve for 1-2 years in diverse, defined capacities such as supervised or stand-alone teaching, student advising, coaching and performing a number of traditional day-school responsibilities. Experienced teachers will mentor, support and provide guidance to the fellow.

All interested candidates should apply online by selecting the Apply for a Faculty/Staff Position above.

Please include a cover letter with your application with expressed interest in either Middle or Upper Schools and indicate area aside from academic expertise that would serve the school, e.g., athletics, fine arts, robotics, community service etc. A Bachelor's Degree is required. Relocation assistance available.

Manager of Marketing and Communications

Manager of Marketing and Communications

The Manager of Marketing and Communications is responsible for all communications, marketing, web-based social media, and graphics at Trinity Prep and reports to the Director of Advancement and Director of Admission, creating plans to deliver key messages and reinforcing the mission and core values of Trinity Prep.

The Manager will participate in and/or oversee the following:

  • Implementation of the communication plan, incorporating consistent themes that support the strategic priorities established by the Head of School and Board of Trustees.
  • Manage the integration and oversight of the school's internet presence, including the website and social media sites, and work with program managers, parents, and Board to ensure that domain-specific web pages are current and consistent.
  • Design and coordinate content and manage all communications for external constituencies.
  • Maintain, prioritize, and implement, in cooperation with the appropriate department directors, overall project lists for website planning, upgrades, and ongoing requests.
  • Manage contracts with vendors to ensure that projects meet deadlines and are within budget.
  • Oversee the production of all school publications and published materials to assure visual and editorial consistency and lend counsel and assistance in the production of collateral material for school events.
  • Maintain a brand identity, including evaluating current communications components, gaining consensus on the school's needs and direction.
  • Evaluate and pursue marketing, external relations, media relations, and advertising opportunities.
  • Manage the communications budget as well as the collection of photographs and videos for the school's website.
  • Supervise the marketing specialist/associate.
  • Create communications plans for key events including invitation design schedules, social media plans, and email campaigns.

The Manager of Marketing and Communications will serve as writer, editor, web-based communicator, production coordinator, and often, graphic designer. As a result, the successful candidate will have a wide cross-section of skills and professional experiences.

The Manager of Marketing and Communications should have:

  • Three to five years of relevant full-time experience in marketing, public relations, communications, and publications project management in a corporate or educational setting.
  • Excellent writing, editing, and organizational skills.
  • Attention to detail.
  • Strong leadership and interpersonal skills, allowing one to work effectively with colleagues and constituents, solve problems, and represent TPS in the community.
  • Experience managing marketing professionals in a fast-paced and vibrant independent school environment.
  • A bachelor's degree or higher, preferably in marketing, communications, public relations, or a related field.
  • Experience in an independent school environment preferred.
  • A strong understanding of the uses and basic mechanics of electronic media, including search engine optimization, geotargeting, and pay per click.
  • Ability to be a self-starter and work independently, meet deadlines, and manage multiple projects at once.
  • Excellent computer skills, including knowledge of current desktop publishing software, preferably Adobe InDesign, Illustrator, and Photoshop.

To apply for this position, please select Apply for Faculty/ Staff Position above.

Qualified Substitute Teachers

College Counselor

Trinity Preparatory School, a coed school for 855 students in Winter Park, Florida seeks an engaging and outgoing College counselor to support students and their families through the college application and scholarship process. Trinity Prep College Counselors work with students formally in the freshman year and continue to do so through senior year within a series of grade-level meetings and workshops in addition to the individual meetings which occur with increasing frequency as the student approaches the application process. Similar to other independent schools, Trinity Prep recognizes that the college application process is part of a family dynamic, and each of our counselors is expected to meet with parents (with and without the student) at scheduled and as-needed meetings.

Primary responsibilities for 45-50 seniors and 45-50 juniors include:

  • Develop college lists to meet student (and family) needs and expectations, and advise students (and family) on the best potential college fit as linked to their academic, athletic, artistic, and family outlook
  • Write and provide counselor recommendation letters for approximately 45-50 seniors
  • Review, edit and support the development and writing of resumes, college essays and applications, and scholarship applications
  • Model and teach interview skills

Additional key duties include

  • Sophomore College Counseling Coordinator
  • Introduce and support Naviance usage
  • TPS Summer/Enrichment Opportunities
  • Maintain a student advisory group
  • TPS Scholarship Coordinator
  • Other duties as assigned: possibilities include direct or shared coordination of the PSAT, School Profile, Students with Special Disability Accommodations, College Handbook, publications, etc.)
  • Develop and lead a college-tour trip.

This is an exempt, 11 month position that runs from August 1 through June 30. Additionally, the position will teach 1 academic section or coach a sport.

Apply Now

Head of Upper School

The Head of Upper School, or upper school principal (HUS) is responsible for all duties attending the planning and supervision of daily life of the upper school students (grades 9-12) and faculty. The Head of Upper School/ Principal reports to the Associate 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 in assuring that the policies of the Board of Trustees are pursued in this division.

Other duties and responsibilities of the Upper School Principal are to:

•communicate the goals and philosophy of the upper school

•consult with parents when necessary with regard to or on behalf of students and/or teachers

•oversee upper school extra-curricular activities and the scheduling of upper school events

•with advisors, counsel students on academic and co-curricular choices, and social activities

•refer students to Upper School Guidance Counselor for testing and/or counseling

•support the Chaplain in the administration of upper school community service efforts

•lead and oversee upper school assemblies and programs

•monitor student behavior and ensure the enforcement of the discipline system

•teach a class and serve as an advisor

  • assist in the hiring, assignment of responsibilities, and evaluation of professionals for retention and advancement

Oversight responsibilities include:

College Counseling (shared with Associate Head of School)

Dean’s Office (discipline)


Administrative support personnel

Student Publications

Student Activities Coordinator, Class Sponsors, and upper school Guidance Counselor

Upper School budget

Committee responsibilities include:

Administrative Team

Admission Committee

Curriculum Committee

Liaison with Trinity Parents’ Organization grade-level representatives;

Perform duties as assigned by the Head of School and/or Associate Head of School

Apply Now

Upper School Dean of Students

Upper School Dean of Students

The Upper School Dean of Students reports to the Head of Upper School and is responsible for articulating behavioral standards, monitoring student behavior, and enforcing the discipline system. In addition, the Dean of Students carries out other duties and responsibilities as delegated by the Head of Upper School in support of the mission of the school.

Other, more specific, duties and responsibilities of the Upper School Dean of Students are to:

  • work closely with teachers and administrators to positively influence student attendance, dress code, and general decorum;
  • oversee chaperone policy and protocol for student trips;
  • present serious discipline cases to the Head of Upper School and/or the Honor Council and Discipline Committee;
  • work with teachers on classroom management procedures to minimize the escalation of behavioral issues;
  • maintain database records pertaining to discipline and attendance;
  • counsel students on decision-making and behavioral choice/modification;
  • consult with parents on matters related to student behavior and discipline procedures;
  • supervise students during the school day and assign faculty supervision duties during non-class time periods of the day to ensure the safety and well-being of all students;
  • chaperone upper school dances, athletic events, fine arts events, and other similar activities;
  • teach and/or coach

Apply Now

Coaching Positions

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

Girls Varsity Volleyball Coach

Aquatics Swim Coach

Blue Group – This swim program is designed for children ages 5-10 to begin year round swimming with a minimal commitment that provides the flexibility to participate in other activities. Participants must be able to swim one length of a 25 yard pool. Swimmers in this group experience the fun of competition via the TPA intra-squad meet and local developmental meets. Emphasis is placed on developing positive self esteem, making friends, and learning the sport. Practices are offered M-F for 1 hr.

Pre-Team - Our program is designed to teach children the skills necessary to become more proficient in swimming in a non-competitive environment. The Pre-Team will focus on learning all components of the four competitive swimming strokes (freestyle, backstroke, breaststroke, and butterfly) including starts and turns. The Pre-Team has been designed as an educational, fun, and safe experience for children. We are offering class on Saturdays beginning in September. Class will be from 11:45 am to 12:45 pm.

Job Description

1. Teach children the fundamentals of competitive swimming, which include sportsmanship, stroke technique, and the rules of the sport while keeping a fun and energetic atmosphere.

2. Prepare & coach daily practices for the Blue group & seasonal PreTeam..

3. Weekly newsletter to parents cc a copy to Head Coach

4. Attend all swim meets- all expenses are paid.

5. Bi Weekly Coaches meetings

6. Certifications required or attainable: Ability to pass USA Background check, CPR, First AID, AED, Safety Training for Coaches, Athlete protection plus the required background requirements for Trinity Preparatory School

7. Nightly & weekend coaching is necessary.

Apply above by completing an application under Apply for a Coaching Position

Boys Cross Country Coach

Interested candidates should complete an application by following the link above: Apply for a Coaching Position

Girls Varsity Golf Coach

Boys Varsity Golf Coach

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. You will not be retaliated against for bringing forth a complaint in good faith.

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