Caulfield named as new Wheelock principal

Superintendent Jeffrey Marsden has announced that he selected Holli Caulfield to be the new principal of the Wheelock School.

Caulfield, of Walpole, is currently the principal of the Oakdale Elementary School in Dedham, a position she has held since 2005. She formally accepted her new position on Thursday, April 11.

"We are thrilled that Holli has accepted the position to become the new principal at the Wheelock School," Superintendent Marsden said. "Holli has served as an elementary school principal in Dedham for nearly 15 years. That type of experience is invaluable and we are all excited to see all that her wealth of knowledge as an educational leader will bring to our students, faculty and staff."

Caulfield will begin her new role on July 1 and will be replacing current Wheelock School Principal Donna Olsen, who will be retiring at the end of the school year.

"Principal Olsen has been a tremendous asset to the Wheelock School and Medfield Public Schools since she came to the district in 2012. She retires after over 30 years in education and we wish her all the best in her retirement, knowing that she will always be a part of the MPS family," Superintendent Marsden said. "We had a number of well-qualified candidates to serve as Donna's replacement and we believe Holli will do great to fill that role."

Caulfield began her teaching career in 1990 as a kindergarten teacher at the Old Post Road School in Walpole. She held the position for one year before working as a second grade teacher at the school for the next 10 years. In 2000, she received the Milken Family Foundation National Educator Award.

From 2002-2005, Caulfield was the Assistant Principal at Walpole's Fisher Elementary School and Elm Street School.

She leaves Dedham with a heavy heart, but also with excitement to start a new chapter in her educational career in Medfield.

"I've loved my time in Dedham and I love everyone at the Oakdale School," Caulfield said. "For me personally, after 15 years leading the Oakdale School, it's time for a change and Medfield is a really good fit for me. The school district's philosophy on education is precisely what I am looking for and when I walked into the Wheelock School it just felt like home. As a former second grade teacher I have always held a passion for teaching middle elementary school education and I am really eager to get started and meet all of the students and staff."

Caulfield describes her style as a principal as someone who is an excellent listener who is able to easily connect with both students and faculty.

Caulfield holds a bachelor's degree in early childhood education from Salem State University, a master's degree in education from Lesley University and an advanced certificate in Pre-K-12 educational leadership from Boston University.

She lives in Walpole with her husband and four children, ages 16, 15, 12 and 11. She loves to travel and spend time with her family and her new job in Medfield will bring her closer to home.

Superintendent Marsden thanked the 33 candidates who applied for the job and the search committee made up of parents, teachers, school committee members, administrators and community members.

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