Benjamin Courchesne

Questioner
DISC Type : c

Head of School at Trinity Valley School

New York City Metropolitan Area, United States

Overview

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.

Personality Overview

Cautious & Analytical

Systematic

Value Seeker

It is quite likely of them to ask for pricing or other concessions.  They prefer to analyze every situation thoroughly.
 While they don't hesitate to ask questions, they are generally risk-averse and tend to be late adopters.

Topics They Care 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.
Teacher Development
Focuses on peer-driven growth for educators, highlighted by his Ainslie Fellowship research on authentic teaching and learning programs.

Media Appearances

Trinity Valley School is excited to welcome their new Head of School, Benjamin Courchesne. Featured in Education Group

See Now

Work History

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

Education

2013 - 2015
Master of Education (M.Ed.) from Teachers College, Columbia University
2008 - 2012
Master of Arts (M.A.) Breadloaf School of English from Middlebury College

More Information

Social Presence :

Prographics :

Exp : 22 Location : New York City Metropolitan Area, United States Job Level : Mid-senior Designation : Head of School at Trinity Valley School
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Insights For Selling To Benjamin

During A Call Or A Meeting

DO's

  • Emphasize on objective proof of ROI, help them do a thorough evaluation
  • Keep some extra margin in hand as they will likely negotiate the pricing
  • Back up any claims with data and numbers

DONT's

  • Don’t overhype the product/pitch, keep it measured
  • Avoid rushing them, be polite and patient
  • Don’t depend too much on anecdotal evidence, it reduces their confidence

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Benjamin is

  • Ensuring that the product delivers ROI, cost-effective pricing and process compliance are very important for them.
  • Will you ever get a clear answer from Benjamin

  • It doesn’t come naturally to them but they can say no if they are not convinced.

Insights For Deal Planning

    How fast (or slow) will Benjamin move?

  • If they have the information that they need, they can move fast at making their decisions.
  • Can Benjamin take some risk or not?

  • They can take risk if they are convinced that they have analyzed the circumstances well.


You And Benjamin

Personality Compatibility


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