For more than two decades, Randy Bertin has been a leader in independent boarding schools and has been a Head of School for over ten years. He is currently the Head of School at Cushing Academy in Ashburnham, Massachusetts. Before Cushing, he spent twelve years at Besant Hill School of Happy Valley in Ojai, California, serving seven of those years as Head of School.

Before Besant Hill, Randy had a seven-year career at Stoneleigh-Burnham School in Greenfield, MA, serving in many roles including Certified Athletic Trainer, Residential Faculty, Teacher, Coach, Dean, Director of Athletics, and Development Officer. Before becoming Head of School at Besant Hill, Randy served in multiple leadership positions there, including Director of Admissions and Financial Aid, Director of Advancement, and Assistant Head for Advancement. He also served as the school’s Varsity Basketball Coach from 2007-2011, earning back-to-back CIF Southern Section championships and CIF-Southern Section Division V coach of the year in 2010. During his tenures as Head of School, Randy has been recognized for his transformative leadership at Besant Hill and is one of only two independent school heads to receive the CASE District VII CEO Leadership Award (2017). He was also awarded the honor of Head of School Emeritus at Besant Hill (2018). Randy is an expert in School Leadership, International Fundraising, and Boarding School Admissions and has presented several times on these topics.