Sara Dingledy selected to be regional high school principal

In this file photo, Sara Dingledy, newly chosen MVRHS principal, met with Islanders in the library conference room earlier this month. – Photo by Cathryn McCann

Superintendent of Schools Matt D’Andrea announced Friday that he had selected Sara Dingledy, current principal of Westchester Square Academy in New York City, to be the next principal of the Martha’s Vineyard Regional High School.

“Sara received tremendous support from those who both served on the search committee and those who had the opportunity to meet her when she visited the high school on January 15th,” Mr. D’Andrea said in a press release Friday. “She demonstrated a clear educational vision and an understanding of the core academic skills that we want our students to master.”

Mr. D’Andrea said Ms. Dingledy “exhibited the leadership skills necessary to turn a vision into an action plan that results in student achievement.”

Ms. Dingledy is expected to move to the Island with her husband and two children in July. “I am excited to have Sara leading the high school and as a member of the Island’s educational leadership team,” he said.

Mr. D’Andrea thanked those involved in the search process, and said the feedback was “tremendously helpful” in making the final decision.

The decision followed a lengthy search process that began in September.

Relief and excitement

In a conversation with The Times on Friday, Ms. Dingledy said she was excited and relieved by the offer. She said she’s looking forward to the move, both professionally and personally.

“I know the kids are very excited to start school out there, and my husband and I are just thrilled to start to get to know the community and put down our roots and settle in there,” she said.

Ms. Dingledy looks forward to getting to know the “fantastic” educational community of teachers, principals, counselors, administrators, and support staff.

“I’m excited to get to know them and think about how we can improve what is already a great place,” she said.

Ms. Dingledy said she plans to use the time between now and July to search for temporary housing, with the ultimate goal of purchasing a house.

Long educational career

Ms. Dingledy has a lengthy resume. She founded the Westchester Square Academy in 2012 as a part of a New York–based program, “New Leaders for New Schools,” an initiative for educators to start their own New York City high schools. Previously, Ms. Dingledy was assistant headmaster of the the Brooklyn Latin School, a social studies teacher, and one of three founding teachers of the Martin Luther King Jr. High School of Art and Technology. She grew up in Connecticut, but has been working in the New York school system for 17 years.

Talking to a small group of community members on Friday, Jan. 20, she said she strives to graduate students who can recognize and show gratitude, have a sense of optimism, find ways to be kind, deal with frustration, and reflect on personal goals, in addition to core academic skills. At that time she said she loves the community, and sees it as a great place to raise her children, ages 3 and 4.

She also has familiarity with the Island. She comes to the Vineyard with her family to visit her uncle, Chuck Wendel of Edgartown, once or twice a year, she said.

“I will say that my big thing is that it’s a big jump — what I do day to day would be very different if I were to come here,” she said at that time. “There’s no perfection in this work. I like to underpromise and overdeliver, and part of that is that there’s not a recipe or a system or a plan that you can come in and drop in. I’m very cognizant of that. It’s a process, and that’s what I like about the job.”

Unexpected job opening

The search process began following the unexpected departure in August of Gil Traverso, who resigned to take a job in the New Haven, Conn., school district one year into a three-year contract. School officials tapped former MVRHS Principal Margaret “Peg” Regan, who retired in 2008, to fill in for one year. A comprehensive search group was put together earlier this fall.

Over the course of several months, the committee reviewed 20 applicants. Interviews were offered to eight candidates, and one declined. From there, school leaders named three finalists in December. One of the three, David Fabrizio, principal of Ipswich Middle School, dropped out of the running shortly after being named a finalist.

David Williams, the other finalist and the former principal of York Middle School in Maine and Ms. Dingledy each visited MVRHS in January. Following that, Mr. D’Andrea reviewed input from the school community, traveled to each candidate’s schools for site visits, and made the final decision.