Benjamin Courchesne in

Benjamin Courchesne

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Head of School at Trinity Valley School
📍 New York City Metropolitan Area, United States

Benjamin Courchesne is the Head of School at Trinity Valley School, bringing over 20 years of experience as a strategic and innovative leader in independent schools. An alumnus of Teachers College, Columbia University, he has a proven track record as a team builder and communicator, previously serving as Head of Upper School at St. Andrews Episcopal School.

As a first-generation high school and college graduate, he is a firm believer in the transformative power of education. He is passionate about making school a meaningful and fun experience for students, often shadowing them for a full day to understand their perspective. He is also an award-winning former lacrosse coach.

He received a one-year Ainslie Fellowship to research and implement an authentic, peer-driven professional development program for teachers.

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Experience
22 Years
Current Role
Head of School
Job Level
Mid-senior
Location
New York City Metropolitan Area, United States
Personality Overview

How Benjamin shows up

Communication Style
Decision Approach
Work Preference

Behavioral traits and communication patterns that shape how this person evaluates opportunities, builds trust, and makes decisions in professional settings.

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Priorities

Topics Benjamin cares about

Student-Centric Education
Believes in making school a meaningful, fun, and vital experience, demonstrated by his practice of shadowing students for a full day to gain their perspective.
Educational Leadership
Has over 20 years of experience in independent schools, holding key leadership roles such as Head of School and Associate Head of School.
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Career

Work history

7-2025
Head of School
Trinity Valley School
7-2023 - 6-2025
Associate Head of School
The Pingry School
6-2020 - 6-2023
Head Of Upper School
St. Andrew's Episcopal School
9-2017 - 6-2020
Co-Site Director Mastery Transcript Consortium
Episcopal High School
7-2016 - 6-2020
Associate Dean of Students
Episcopal High School
In the press

Media appearances

Trinity Valley School is excited to welcome their new Head of School, Benjamin Courchesne. Featured in Education Group
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Education
2013 - 2015
Master of Education (M.Ed.)
Teachers College, Columbia University
2008 - 2012
Master of Arts (M.A.) Breadloaf School of English
Middlebury College
Social presence
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Behavioral profile

DISC profile (public)

DISC behavioral profile

Dominance, influence, steadiness, and calculativeness scores with guidance on how this person prefers to communicate and decide.

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