Holli Caulfield, MEd

Holli Caulfield is an accomplished education professional with a B.S. in Early Childhood

Education from Salem State University, an M.Ed. in Educational Technology from Lesley

University, and studies in Educational Leadership from Boston University/The Education

Collaborative. She holds multiple Massachusetts licenses, including Superintendent/Assistant Superintendent and Principal Pre K-6, along with a Teacher License for Early Childhood: Students with and without disabilities K-3.

Since 2019, Holli has been the Principal of Ralph Wheelock School in Medfield, MA, where her leadership skills have been instrumental in managing nearly 400 students and over 60 staff members. She excels in supervising educational programs, maintaining student discipline, and coordinating cultural arts and standardized testing initiatives. Her strategic leadership during the transition to remote learning and collaboration on school improvement plans further demonstrate her capacity to drive school-wide success. Concurrently, she mentors aspiring principals as a Faculty Member and Principal Candidate Supervisor at the Education Leadership Institute (ELI)/ACCEPT Collaborative.

Holli's extensive career includes 14 years as Principal of Oakdale Elementary School in

Dedham, Massachusetts, where she led a significant renovation project to create a

state-of-the-art Computer Lab and Media Center. Her ability to inspire and manage teams is evident from her time as an Assistant Principal and classroom teacher in Walpole, Massachusetts. Holli's leadership excellence has been recognized with awards such as the Milken Family Foundation National Educator Award and the Department of Education Lighthouse Grant. She is also an active member of professional organizations serving on the board for MassCUE as well as 2 terms on the Department of Education Principal Advisory Board.

Outside of work, Holli enjoys cycling, traveling, and spending time with family and friends.