Randy Richardson

Randy Richardson

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Randy Richardson

Randy has strong ties to Oliverian. Not only did he lead Oliverian between 2009 and 2014, but his son, Josh, is also a graduate.

Randy has over 30 years of experience as a teacher, coach, and administrator of independent schools. He earned his B.A. at Hamilton College and his MALS Degree from Wesleyan University. In addition to running a boarding program at Shady Side Academy in Pittsburgh, Pennsylvania, he served as Head of School of The Derryfield School in Manchester, NH. Randy also worked for two years as an educational and nonprofit consultant for Breakthrough Collaborative, a national students-teaching-students program dedicated to educational equity and teacher training.

After leaving Oliverian, Randy decided to fuse his love of the outdoors and the Upper Valley with his experience as an educational administrator and fundraiser. He is now development director for the Upper Valley Trails Alliance, and organization focused on advocating for trails to provide access to nature and better health. Randy lives and hikes with his family and dogs in Woodstock, Vermont.

What do you love most about Oliverian?

“I love that Oliverian strives to acknowledge and embrace the true uniqueness of every student stepping onto the beautiful campus. When so many educators and specialists are trying to find THE ‘formula’ or ‘system’ to solve all of our social and educational problems, Oliverian has intentionally bucked this flawed cookie cutter trend. The dedicated staff members at Oliverian understand that they cannot possibly know how to truly inspire and help a student until they genuinely know that individual as a unique human being. While they are informed by history and perception of others, they are primarily driven by who the student is at Oliverian at that moment. This kind of fresh start is an incredible gift given almost daily at Oliverian.”