Independent Thinking was founded in 2000 by independent school professionals
Meet The Team
Jane Armstrong,
Founder & Managing Partner
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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.
Samantha Sawin Brennan,
Senior Consultant
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Samantha Brennan joined Independent Thinking in 2023, bringing over 25 years of experience in independent schools. Most recently, she served as Assistant Head of School and Dean of Faculty at St. Mark’s School (MA) for six years. Before St. Mark’s, Samantha spent 15 years at The Rivers School (MA), where she began as School Counselor and Director of Wellness, taught Leadership, and held the role of Dean of Upper School Students. She began her career teaching Biology and Chemistry at the Delbarton School (NJ). Samantha has been an active leader in independent school education, serving on the leadership team of the Gardner Carney Leadership Institute for many years and presenting at regional and national conferences on leadership and faculty development. Samantha earned her MBA with a focus on Strategy and Management from Babson College in 2022, holds a Master’s of Education in Human Development and Psychology from Harvard University, and received her undergraduate degree in Biology from Georgetown University. She is an alumna of The Agnes Irwin School (PA). Samantha lives in the Boston suburbs with her husband and their twins who currently attend the Fay School.
The IT Commitment
We will...
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Work hard and well for you
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Value your school's resources
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Listen well and respect your school's individuality
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Connect you with great candidates