Educator Profile    Educators

Holli Armstrong (MA '00)


Ralph Wheelock School
Medfield, MA

Subject(s) taught: Principal
Grade(s): 2, 3

At the time of the Award, Holli Armstrong was:

Old Post Road School
East Walpole, MA

Subject(s) taught: General Elementary
Grade(s): 2

Biographical Information

Holli Caulfield was the principal of the Oakdale School in Dedham MA from 2005-2019. She began her principalship in 2005. One of her most notable accomplishments at Oakdale was the renovation of the third floor of the school. The building is more than 100 years old and the 3rd floor was not used in over 50 years. With the help of parents and community partners a state-of-the-art library/media center was created. The project was done strictly by volunteers. Prior to becoming an administrator in Dedham, Caulfield was an assistant principal in Walpole, MA. 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. While at the Old Post School, she also wrote and received a Lighthouse grant from the Massachusetts Department of Education, was a member of the K-12 Technology Steering Committee, and was featured in a Department of Education video on technology-integrated instruction. In addition to directing Walpole's Summer Academy for K-6 students and co-creating a before-school choral program, Caulfield served on the board of the Walpole Teachers Association and was instrumental in implementing a more inclusive collective bargaining system. Caulfield was also the recipient of a Milken Festival for Youth grant in 2004, creating an environmental classroom.

In July of 2019, Holli became the principal at the Ralph Wheelock School in Medfield.

Related Connections

Milestone: Holli Armstrong (MA '00) Named to Executive Teaching Board

Additional Information


Boston University, Ed. Leadership

Lesley University, M.Ed