Trinity Prep is excited to post job openings for the 2025-2026 Calendar Year. As we “Build for Tomorrow,” the administration is looking to better the Saints community in many ways by investing in its teachers, beautifying the campus and more. While this is a post about employment opportunities, I want to take this opportunity to mention the NEW Nochur Sankar Science Building. It should be the #1 reason you or anyone should come to the Trinity Preparatory School OF FLORIDA. PLEASE make sure that you know that this is Trinity Prep in Winter Park, FLORIDA before applying.

   Job Postings:

   Assistant Head of Aesthetic Uniformity and Punctuality Regulation (AHOAUAPR)

   Trinity seeks an uptight, strict individual who will ensure that kids remain orderly. Resembling the Dolores Umbridge of Trinity Prep, any applicant for this role must love order and order only. Epitomizing a goody two shoes, your sole job is to ensure that students have detention at least once in their life and follow the 700-page Student Handbook which we expect you to recite from memory. Most of your day will be spent perched upon the rock, like a hawk, with binoculars in one hand and a speaker phone in the other. 

   If a shirt is untucked, you must swiftly give the individual in question seven detentions and berate them for their disorderly conduct. If a student is tardy, they will not be able to attend class. Our sole hope is that students will leave Trinity knowing that showing your shoulder or lacking a belt has no place in this preparatory school.

   Associate Assistant Head of the Upper School’s Upperclassman (AAHOTUSU)

   Trinity seeks an administrator whose sole job is to police the upperclassman. In their young adult era of challenging authority, you must keep them in check. Specifically, under no circumstances should we allow students to dance zestily, put paint in our hair or dare throw a water balloon at a 6th grader. It is against our mission and our values. 

   Supreme Grand Premier Master Fellow (SGPMF)

   Similar to a Master Teacher, a title provided to only three teachers on campus, a Master Fellow is a distinguished, qualified individual we hope to develop to become an expert teacher. Similar to an intern, you will be paid in coffee, receive seasonal pies, and must coach 5 sports and 7 extracurriculars. This will provide you with the skills to excel in the real world. Looking forward to helping you grow!

   Consultant to the Head of School on Happiness Maximization (CTTHOSOHM)

   Trinity seeks to create a happy community to cultivate the ethical, resilient leaders of tomorrow. Hired from McKinsey, Deloitte or Boston Consulting Group — we hope you can aid our school and help our students become consultants in the future. 

   You will analyze the impacts of Grille panini prices on student welfare, the generational impacts of sod on students’ feet, and provide a prospectus for the 2025-2026 Bocce Ball season.