Eaglebrook School has a faculty of 74 men and women, many of whom have young, school-aged children of their own. Classes average between eight to twelve students, and teachers help each boy establish sound study habits and set standards for quality work.
Eaglebrook's faculty have chosen to focus on junior boarding school education for boys. Our teachers have the skills to make learning fun and engaging for middle school boys while supporting them with the structure and guidance they need. They recognize where boys are in their social, emotional, and intellectual development and appreciate them for who they are.
  • Photo of Andrew Parsons
    Mr. Andrew Parsons
    Teacher; Dormitory Advisor; Coach
    Biography
     
    Drew Parsons is a recent graduate from the College of the Holy Cross where he double majored in both Economics and Spanish. Being an Eaglebrook graduate himself, he is familiar with the unique environment that the school offers and is excited to share his experience with the students. He looks forward to introducing the Harkness method to the Math Department, a form of learning he connected strongly with during his time at Phillips Exeter Academy. Outside of the classroom, Drew will coach Thirds Soccer and live in Flagler House. When not working, he loves hiking in the White Mountains, playing sports, and watching movies. 
  • Photo of Karen Pleasant
    Mrs. Karen Pleasant
    Chair of the History Department; Dormitory Advisor
    Biography
     
    Karen joined Eaglebrook in 2021 as a teacher, coach, and advisor. She currently serves as the History Department Chair and out-of-dorm advisor for Halsted House and advises the Debate Club. Karen came to the Hill from the Stoneleigh-Burnham School in Greenfield, Massachusetts, where she spent 12 years as the History Department Chair, co-coordinator of the International Baccalaureate program, and debate coach. Prior to her time at Stoneleigh-Burnham, Karen spent nearly a decade at the Northfield Mount Hermon School. She holds a Bachelor of Arts degree from Skidmore College, where she was a double major in history and political science, and earned her MAT, with a concentration in history, from Smith College.

    In her free time, Karen loves spending time on the water and is currently a member and competitor in the New England Canoe and Kayak Racing Association and co-coach of the Paradise City Dragon Boat team—a team of cancer survivors and supporters. She and her husband, Tod, who is Eaglebrook’s Technology Project Manager, live in Greenfield with their dog, Darwin.
  • Photo of Tod Pleasant
    Mr. Tod Pleasant
    Technology Project Manager; Teacher; Coach; Dormitory Advisor
    Biography
     
    Tod joined Eaglebrook in 2020 as the School's Technology Project Manager. He also oversees Audio Video resources, teaches computer electives, and coaches Mountain Biking in the fall. Tod spent over two decades at Stoneleigh-Burnham School in Greenfield, MA, where he served as the Director of Technology. He is an avid mountain biker, writer,  podcaster, and has too many random hobbies and interests to list. He and his wife, Karen, a member of Eaglebrook’s History Department, live off-campus in Greenfield with their dog, Darwin. 
     
  • Photo of Jaye Pope
    Ms. Jaye Pope
    Teacher
    Biography
     
    Jaye has been teaching Ceramics at Eaglebrook since 2010. As an artist, she has her own studio Good Dirt Pottery in Brattleboro VT, where she and her wife Kathleen live. She is a long time supporter of the Empty Bowls Project which benefits people with food insecurity, and has engaged her ceramics students in creating collaborative pottery donations for the Project. She co-owns the Sawmill River Arts Gallery located in the historic Montague Mill. When not working in clay, Jaye can be found hiking with her dog Mina, volunteering for the Vermont Food Bank, traveling with her family, or riding her Moto Guzzi motorcycle.
  • Photo of Doug Porter
    Doug Porter
    Maintenance Staff
    Biography
     
     
  • Photo of Autumn Porubsky
    Autumn Porubsky
    Counselor
    (413) 774-9257
    Biography
     
     
271 Pine Nook Road   |   P. O. Box 7   |    Deerfield, MA 01342   |   413-774-7411