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Independent Thinking was founded in 2000 by independent school professionals

Meet The Team

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Jane Armstrong, 

Founder & Managing Partner

Jane Armstrong is Managing Partner and a Founder of Independent Thinking, IT. Now in her 25th year at IT, Jane has led or co-led 70 Head of School searches and over 200 searches for other senior administrative positions. Her expertise has been sought for numerous regional association panels, leadership professional development conferences, and for numerous industry publications, including contributing a chapter to NAIS Head of School Search Handbook, 2nd Edition, published 2018. Jane enjoyed 12 years of service in private education before launching Independent Thinking in 2000. She began her career as a "triple threat" English teacher, dorm parent and coach at the Peddie School. She served Peddie as the Director of Publications before returning to her alma mater Amherst College to work in the Alumni and Development Office. Jane helped Amherst achieve fund raising records in dollars raised and participation. She returned to independent schools as the Dean of Students and Director of Residential Life at the Garrison Forest School. She returned to development as the Director of Development at Chapel Hill-Chauncy Hall School, raising record dollars and served a key role in the preparation of a strategic plan. Jane has been an active volunteer for Amherst College, co-chairing her 25th Reunion and serving on the Alumni Trustee Nominating Committee. Jane is an independent school trustee, and the parent of five independent school graduates—and now one teacher.
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Samantha Sawin Brennan,

Senior Consultant

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Samantha Brennan joined the Independent Thinking team in 2023 after spending twenty-five years in a variety of positions in independent schools. In her most recent school position, Samantha served as Assistant Head of School and Dean of Faculty at St. Mark’s School (MA), for six-years. Prior to joining St. Mark’s, Samantha spent fifteen years at The Rivers School (MA). She began her time at Rivers as School Counselor and Director of Wellness, taught Leadership, and served the school as Dean of Upper School. Sam began her career in independent schools teaching Biology and Chemistry at the Delbarton School (NJ). For numerous years, Samantha was on the faculty of the Gardner Carney Leadership Institute, an annual summer institute for independent school educators dedicated to researching, developing, and disseminating the pedagogy of leadership; she has presented regularly at regional and national conferences on a range of topics including leadership and faculty development. Samantha has an MBA, earned in 2022, from Babson College, holds a Masters of Education in Human Development and Psychology from Harvard University’s Graduate School of Education and earned her undergraduate degree in Biology from Georgetown University. Samantha is a graduate of an independent school, is married to a college basketball coach, and they enjoy parenting a set of twins who are currently in middle school.

The IT Commitment

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We will...

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  • Work hard and well for you

  • Value your school's resources

  • Listen well and respect your school's individuality

  • Connect you with great candidates

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