Summary
Overview
Work History
Education
Teaching
Professional Development
Research And Writings
Awards
Languages
Timeline
Hi, I’m

Tiffany D. Trotter

New York,NY
Tiffany D. Trotter

Summary

Educational leader who combines academic expertise with executive management skills to advance independent schools. Track record of implementing strategic initiatives that strengthen enrollment, enhance fundraising, and improve academic programs. Successfully directed $3M capital projects, secured International Baccalaureate candidacy, and maintained enrollment during challenging market conditions. Strong record of building systems, developing programs, and fostering community cohesion. Combines educational vision with practical leadership to guide schools while preserving institutional values and maintaining focus on academic excellence and fiscal sustainability.

Overview

22
years of professional experience

Work History

The Guild of Independent Schools of New York

Member, Board of Directors
01.2023 - Current

The Kew-Forest School

Interim Head | Head of School
07.2022 - Current

Job overview

  • PS-12 school of 200+ students, 73 employees, and $8.6M annual operating budget
  • Spearheaded $3 million campus redevelopment project across 10,700 square feet of a historic Georgian campus, renovating 13 classrooms, 7 offices, and 4 specialized spaces across multiple wings (lower school, upper school, library, laboratory building, and gymnasium/auditorium) while maintaining full school operations over 1.5 years on our two-acre campus
  • Directed successful candidacy process for International Baccalaureate World
  • School status (PYP & MYP), positioning school for 2025 authorization
  • Increased enrollment by 12% in one year through strategic admissions initiatives while reducing tuition discount rate from 60.1% (SY24/25, 50 students) to 22.4% (SY25/26, 42 students) for newly admitted students
  • Led digital marketing initiatives that drove 30-65% year-over-year growth in, Business Profile interactions across all metrics, including a 111% increase in website clicks and 102% increase in engagement during critical enrollment periods, significantly enhancing visibility and prospective family outreach
  • Launched comprehensive rebranding initiative including new website development and marketing strategy; secured Board and alumni donor support to expand marketing budget; contracted strategic marketing partner (AiMS) to elevate digital advertising capabilities with first-ever implementation of A/B testing across creative elements and CTAs, multi-channel campaign management, and enhanced, Business Profile optimization, resulting in improved digital presence and lead generation
  • Enhanced fundraising effectiveness: in a school building its culture of philanthropy, increased parent donations by 100%, grew total donations by 50%, and expanded donor base by 53% within 6 months; secured school's first endowed gift ($25,000)
  • Implemented enterprise-wide security enhancement program encompassing both physical and cyber infrastructure
  • Strengthened governance by expanding board membership by 30%, adding expertise in education and entrepreneurship, enhancing board functionality and diversity

The Kew-Forest School

Head of Middle & Upper School
07.2018 - 06.2022

Job overview

  • Directed academic division serving 150 students in grades 6-12 with 24 faculty members and $6.5M budget
  • Enhanced student support in 2018 through comprehensive mental health program implementation including, Program (Yale Center for Emotional Intelligence) and full-time counseling services
  • Developed proactive COVID response, preparing faculty and students for remote learning before citywide shutdown, resulting in hybrid in-person and remote learning for SY20/21 and consistent enrollment during the height of the pandemic (2020-2022) in contrast to national trends (2-9% loss in small schools)
  • Introduced project-based learning to enhance Middle & Upper School program
  • Created and refined operational systems that improved efficiency and accountability in course enrollment, graduation tracking, and student services

Avenues: The World School

Associate Division Head
07.2016 - 06.2018

Job overview

  • Co-led divisional leadership team overseeing 200+ students and 50+ faculty
  • Transitioned pedagogy to project-based learning, resulting in [specific outcome - student performance increase/engagement metric]
  • Implemented comprehensive faculty evaluation system that informed professional development and improved instructional quality

Avenues: The World School

Head of Grade
07.2012 - 06.2016

Job overview

  • Alongside the Division Head, was one of two founding administrators for the Upper School
  • Served as founding Head of Grade for inaugural high school class, growing from 42 to 56 students(+25%) in four years, and shepherding students to top colleges including Stanford, Yale, and the University of Chicago
  • Partnered with senior leadership to shape institutional culture during critical growth phase,expanding from one grade (42 students) to a full high school (200+ students)
  • Developed comprehensive grade-level programs aligned with school's global vision
  • In a start-up school environment, developed all systems necessary for running a school
  • Built partnerships with key stakeholders including parents, faculty, and administrators, building faculty cohesion and parental buy-in for curriculum and programming

Phillips Exeter Academy

Leadership & Program Development
09.2003 - 06.2012

Job overview

  • Director of Junior Studies Program, leading interdisciplinary team of 10+ faculty members from 9 departments, teaching a required 9th grade course; conducted comprehensive curriculum overhaul and implementation
  • Served on Principal's Search Committee, one of four faculty members (of 200+ faculty) selected to determine leadership transition
  • Served in key capacities through work on:
  • Appointments & Leaves Committee (evaluating untenured faculty)
  • Agenda Committee (faculty advocacy; was highest vote recipient of 200+ faculty) o Curriculum Committee (successfully revised trimester calendar)

• Dormitory Head (2004-2012) of boys dorm with 40+ students; led team of 5 faculty members and 5 senior proctors

Education

University of Chicago

ABD from U.S. History
06-2001

University of Chicago

MA from U.S. History
06-1997

Stanford University

BA with Honors from U.S. History
06-1996

Teaching

Avenues: The World School, New York, NY | 2012-2016

  • Humanities History (World History, US History), 2012-2016
  • Life Skills, 2012-2013


Phillips Exeter Academy, Exeter, NH | 2003-2012

  • Junior Studies (9th grade required course)
  • US History (11th grade required course)
  • Electives: 20th Century World History (9th grade) | Japan: Tradition to Modernity (9th/10th grade) |Classical Greece (9th/10th grades) | Classical Rome (9th/10th grades) | Medieval Worlds (9th/10th grades) | Early Modern Europe, 1350-1660 (10th grade) | Absolutism & Revolution, 1660-1800 (10th grade)
  • Club Sports (open to all grades): Social Dance | Ultimate Frisbee


The Latin School of Chicago, Chicago, IL | 1999-2003

  • Humanities (9th grade) | US History: A Survey through Different Voices (11th grade)
  • Electives: African Civilization (10th grade) | Gender at the Crossroads (11th/12th grades) | Race in American History (11th/12th grades) | World History (12th grade)

Professional Development

  • NYSAIS Heads Conference, 2022, present
  • NAIS Institute for New Heads, 2022, 2022
  • International Baccalaureate Workshop: Leaders Engage the Community, 2025, 2025
  • International Baccalaureate Workshops Category 1 Trainings for Heads of School, 2023, 2023
  • NAIS People of Color Conference Steering Committee, 2002, 2002

Research And Writings

  • "Alternative Race Relations? Indians, Blacks, Mixed-Blood Offspring, and Identity Creation in Indian Territory, 1880-1920," Dissertation Proposal, 2001
  • "On Gentility, Uplift and Segregation: Manners and Old Settlers' Response to the Great Migration in Chicago, 1917-1919," Second-year Seminar Paper, 1998
  • "Beginning the Conversation: An Exploratory Examination of Indian-Freedmen Relations in Indian Territory, 1866-1907," Master's Thesis, 1997

Awards

  • Pease Fund Awardee, First recipient of this award intended to sustain and enhance history faculty through immersion experiences., Phillips Exeter Academy, 2011
  • Stanford University's Teacher Tribute, Nominated by a former student, granted by Stanford in recognition of exceptional teaching and dedication to the field of education., Stanford University, 2009
  • Dr. Daniel E. Koshland, Jr., Class of 1937 Distinguished Faculty Fund, Award to recognize faculty whose innovation, creativity and dedication inspires and stimulates students to strive for academic excellence., Phillips Exeter Academy, 2008
  • Dormitory Adviser Award, Given to someone whom students trust and regard as caring and concerned for the kind of human beings they are and can become., Phillips Exeter Academy, 2007

Languages

Spanish
Full Professional
French
Limited Working

Timeline

Member, Board of Directors

The Guild of Independent Schools of New York
01.2023 - Current

Interim Head | Head of School

The Kew-Forest School
07.2022 - Current

Head of Middle & Upper School

The Kew-Forest School
07.2018 - 06.2022

Associate Division Head

Avenues: The World School
07.2016 - 06.2018

Head of Grade

Avenues: The World School
07.2012 - 06.2016

Leadership & Program Development

Phillips Exeter Academy
09.2003 - 06.2012

University of Chicago

ABD from U.S. History

University of Chicago

MA from U.S. History

Stanford University

BA with Honors from U.S. History
Tiffany D. Trotter