Holli Caulfield, MEd

Holli Caulfield is an accomplished educational leader with extensive experience in school administration, instructional leadership, and educator development. She holds a B.S. in Early Childhood Education from Salem State University, an M.Ed. in Educational Technology from Lesley University, and has completed studies in Educational Leadership through Boston University/The Education Collaborative. She holds multiple Massachusetts licenses, including Superintendent/Assistant Superintendent, Principal PreK–6, and Early Childhood Teacher (Students With and Without Disabilities, PreK–3).

Prior to her retirement in 2025, Holli served for six years as Principal of Ralph Wheelock School in Medfield, MA, where she oversaw nearly 400 students and more than 60 staff members. Her leadership encompassed instructional supervision, school improvement planning, staff development, and school-wide initiatives. She also successfully guided the school through the transition to remote learning. In addition, Holli serves as a mentor to aspiring principals and as a faculty member and Principal Candidate Supervisor with the Educational Leadership Institute (ELI)/ACCEPT Collaborative.

Earlier in her career, Holli spent 14 years as Principal of Oakdale Elementary School in Dedham, MA, where she led numerous school improvement initiatives, including a major renovation to create a state-of-the-art computer lab and media center. She also served as an Assistant Principal and classroom teacher in Walpole, MA, building a strong foundation in teaching, learning, and school leadership.

Holli's contributions to education have been recognized with honors including the Milken Family Foundation National Educator Award and the Department of Education Lighthouse Grant. She has also served on the MassCUE Board of Directors and completed two terms on the Massachusetts Department of Education's Principal Advisory Board. Continuing her commitment to supporting schools and developing educational leaders, Holli currently serves as Interim ETL at Dedham's Early Childhood Center. She brings a wealth of experience, practical insight, and a collaborative approach to her work, helping educators and school leaders strengthen their practice and navigate the challenges of educational leadership.

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