Advancement Fellow (2026-2027)

Trinity Preparatory School; Winter Park (FL); On-site; USD 45,000 - 60,000; Full time

Benefits offered by this job

Medical benefits

Dental benefits

Vision benefits

Life insurance

Disability insurance

Job summary

Trinity Preparatory School of Florida seeks a motivated recent college graduate or a candidate exploring a career in education to join the Fellowship Program. Fellows will serve one to two years in supervised teaching, course observation, advancement activities, and school events, under the guidance of the Assistant Head of School.

Responsibilities include co-advising, mentoring, coaching, and contributing to program development, while completing day-school duties.

Qualifications

• Bachelor's or Master's degree required; strong interest in education.
• Enthusiasm for teaching, mentoring, and student development.
• Willingness to participate in professional development and coaching.

Responsibilities

• Co-teach and supervise teaching activities under mentor guidance.
• Participate in advancement activities, events, and donor relations tasks.
• Assist in athletic coaching and school events (promotions, homecoming, etc.).
• Engage with mentorship programs and professional development opportunities.
• Perform job-related duties as assigned.

Skills

Communication skills

Collaboration

Education

Bachelor's degree

Job description

Available Position: Trinity Preparatory School Advancement Fellow (2026-2027) Department: TBD

Reports to: Assistant Head of School

Full/Part-time: Full-time

Date Posted: 09-21-2026

Start Date: TBD

About the Trinity Preparatory School of Florida:

Trinity Preparatory School is an independent, coeducational, college preparatory school that helps students excel in college and in life, contribute to their communities, lead in a changing society, and grow spiritually. In alignment with our mission, we affirm our commitment to our core values: Trinity Family; Educational Excellence, both Academic and Extracurricular; Leadership and Character Development; and Faith and Spirituality.

Founded 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 the Trinity Preparatory School in grades six through twelve. Affiliated with the Episcopal Church, we welcome families and students from all faith traditions, cultures, and backgrounds, knowing that we are all enhanced by diversity.

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 inside and outside 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.

A full-time Fellow position at Trinity Prep consists of serving as a co-advisor, teaching/advancement duties, coaching, and assuming additional duties as assigned.

Position Summary:

Trinity Prep seeks an enthusiastic recent college graduate or an individual interested in pursuing a career in education to participate in our Fellow Program. Fellows will serve for one to two years in various, defined capacities such as supervised teaching and course observation, participation in advancement and development activities, participation in an outdoor program/school grade level trips, major event execution such as prom and homecoming, student advising, coaching a sport, and performing a number of other traditional day-school responsibilities. Fellows will be supervised by the Assistant Head of School, who will review their performance with the appropriate department head, provide feedback, and further their professional development and training. This position will remain open until filled.

Trinity Prep Professional Values:

Below are Trinity Prep's four Core Competencies that apply to all employees of the organization:

We:

• Demonstrate Self-Awareness
• Ensure Accountability
• Communicate Effectively
• Cultivate Innovation

Trinity Preparatory Fellows will exemplify the following Fellow Leadership Competencies that apply to all participants in the Fellow Program:

• Self-Development
• Interpersonal Savvy
• Instills Trust with a Customer Focus
• Drives Results

Trinity Preparatory Fellows will exemplify the following Coaching Leadership Competencies that apply to members of the Athletic Department:

• Develops Talent
• Directs Work

Trinity Preparatory Fellow Responsibilities:

• Perform supervised and increasingly unsupervised work in a primary area of the school and the Fellow's primary area of interest.
• Share their specialized training, expertise, or talents with the faculty, staff, and students.
• Substitute, teach, team-teach, and/or under the guidance of experienced and skilled faculty.
• Participate in the mentorship program with experienced teachers and staff who will support, guide, and work collegially with Fellows.
• Attend and participate in professional development and training opportunities.
• Coach up to three seasons at appropriate levels of expertise.
• Perform job-related duties as assigned.

Teaching & Coaching Responsibilities:

• Collaborate closely with mentor teachers and head coaches to co-plan, deliver, and facilitate engaging lessons and team practices across both classroom and athletic environments.
• Differentiate classroom instruction and athletic coaching to support diverse student needs, using varied methods (e.g., discussions, demonstrations, skill drills, and guided practice) to foster individual growth, curiosity, and sportsmanship.
• Establish and communicate clear learning and performance objectives for academic units, daily lessons, athletic practices, and game strategies.
• Design, administer, and grade academic assignments and tests while providing ongoing, constructive feedback to students and athletes in the classroom, on the field, and during practices.
• Cultivate physical, social, and emotional safety across all campus spaces—reinforcing core school values, student discipline, sportsmanship, and proper facility/equipment maintenance
• Serve as a positive role model and learn best practices for communicating progress, expectations, and priorities effectively with students, athletes, parents, and guardians.
• Participate actively in mentoring relationships, cohort workshops, and team/department meetings to contribute to program development and build core competencies as an educator and coach.
• Perform job-related duties as assigned.

Advancement Responsibilities:

• Work closely with Advancement leadership across Development, Marketing, and Admissions to gain hands‑on experience in independent school operation, supporting brand messaging, annual giving campaigns, alumni engagement initiatives, and student enrollment initiatives.
• Assist in coordinating and executing key school, alumni, fundraising and admissions events including logistics, student/volunteer coordination and event communications.
• Learn best practices for cultivating donors, conduct prospect research, crafting compelling social media/marketing content, and building positive relationships with alumni, current families, and donors.
• Assist with job‑related duties, school events, and administrative tasks as assigned to gain comprehensive exposure to independent school life
• Perform job-related duties as assigned.

Athletic Teams (Varsity, Junior Varsity, and Middle School) include the following 15 different sports:

Fall

Bowling

Cheer

Cross Country

Golf

Football

Swim and Dive

Volleyball-Girls

Drumline

Winter

Basketball

Cheer

Soccer

Weightlifting- Girls

Spring

Baseball

Lacrosse

Softball

Tennis

Track and Field

Volleyball-Boys

Weighlifting-Boys

Qualifications and Experience:

• Possess a Bachelor's or a Master's Degree from an accredited University or College.
• Promotes an inclusive environment that values, encourages, and supports

differences.

• Possess an enthusiasm for education and learning.
• Possess an affinity for and comfort in working with Middle and Upper School aged children.
• A preferred candidate will have both playing and coaching experience, but one or the other is acceptable.
• Demonstrate competency with student-centered technology, an interest in advancing and supporting its use to enhance student learning, and the desire to employ technology to connect with students who learn both remotely and in-person.
• Demonstrate an interest in contributing to conversations about instruction and curriculum, classroom management, and the stages of childhood development.
• Carry the maturity, interpersonal and social skills to function as a contributing and

responsible member of the faculty.

• Welcome membership and participation in the cohort of the Trinity Preparatory Fellowship, both contributing to and growing from the benefits of membership in this

cohort.

• Demonstrate the professionalism of a full-time educator, demonstrating among other traits, punctuality, initiative, and independence.
• Demonstrate an authentic work ethic and positive spirit.
• Must pass a Jessica Lunsford Level II background check and drug test.

Certifications Required:

• CPR/AED/First Aid can be obtained upon hiring.

Benefits:

• Comprehensive benefits package including medical, dental, vision, life and disability.

Employee Nondiscrimination Policy:

• Trinity Preparatory School is an Equal Opportunity Employer.

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.