Holli Caulfield is currently the principal of the Ralph Wheelock School in Medfield. Before coming to Medfield, Holli was the principal of the Oakdale School in Dedham from 2005-2019. Prior to becoming an administrator in Dedham, Holli was an assistant principal in Walpole. She began her career as a kindergarten and then a second-grade teacher at the Old Post Road School in East Walpole. Mrs. Caulfield was so effective in relaying computer and digital skills to students that they, in turn, taught those skills to adults visiting Caulfield’s classroom regularly. While at the Old Post School, she also wrote and received several Lighthouse grants from the Massachusetts Department of Elementary and Secondary Education. She was a member of the K-12 Technology Steering Committee, and was featured in a Department of Education video on technology-integrated instruction. In 2000 Holli received the Milken Family Foundation Outstanding Educator Award. In 2004 she went on to receive a Milken Festival for Youth grant creating an outdoor environmental classroom. In her free time she enjoys traveling with her husband and children, cooking, and reading.