
As the date to nail down a new educator in one of the top leadership positions on the Island looms, the search committee for the position planned community forums in an effort to hear about the qualities parents and residents want in a new superintendent.
The public events are being moderated by Sean Costello, a representative from the organization leading the search for a new superintendent called the Massachusetts Association of School Committees (MASC). The sessions began this week, from Tuesday, Jan. 13 through Thursday, Jan. 15, at the West Tisbury School, the Martha’s Vineyard Regional High School, and on Zoom.

The first meeting on Tuesday was attended primarily by Island educators. Attendees were asked to write down qualities they’re looking for in a new superintendent, issues they believe are being addressed appropriately by the school system, and issues they want further action on by new leadership.
Costello said all meetings will be similarly structured, and the information gathered will be added to a report that will be public and used to sort through applicants for the position.
“No school district is perfect … but it’s our job to make sure Martha’s Vineyard Public Schools are moving in the right direction,” Costello said to the group on Tuesday.
The search for a new leader of Vineyard schools is just entering the public eye. The current superintendent of schools, Richard (“Richie”) Smith, announced a few months ago that he’ll be retiring in June 2026 after a 25-year career as an educator. According to Alex Salop, the newly elected chair of the search committee to find someone to fill the role, no one has jumped out as an obvious candidate yet.
The deadline for applications for the new superintendent of schools is Jan. 21, and according to school officials, about five have been received so far. Some qualifications include a master’s degree, 10 years of education experience, and a preference of five years of work in a central school office. Finalists will be interviewed in early February, and a decision will be made by the All-Island School Committee on Feb. 12.
As the applications trickle in, Salop said he’s turning to the community for qualities they hope to see in a leader. For the search committee, which is made up of 19 representatives from across the Island, there are some nonnegotiables. Support for the socioeconomic, racial, and ethnic diversity of the student body, budgetary concerns, and juggling five school districts on one Island are just a few of the needs that stick out for Salop and the search committee.
“We have a diverse community on the Island, including a large immigrant community, and all of these people need to be served well,” Salop said in an interview with The Times. “It’s really important to hear from the community before making decisions on things like this.”
According to enrollment data from this school year, more than 30 percent of the student body across Vineyard schools speaks a first language other than English. The Vineyard also has a higher population of Native American students compared with the state, at nearly 2 percent of the population. In addition, more than half of students are “high needs,” a group that includes low-income students, English language learners, and students with disabilities.
The new superintendent will also have to juggle five school districts and six towns, including the multiple budgets and school committees that go with each. Salop noted the high cost of living and low availability of housing, which are concerns of the search committee as they look for candidates from across the country. The position doesn’t come with a housing guarantee, and although the salary is a competitive rate, at a range of $185,000 to $240,000, a home can be difficult to find, even for the most seasoned year-round residents.
“We have budget issues because of how many districts we have on the Island and the duplicative nature of education on the Vineyard … not to mention how much it costs to live here,” Salop said.
While talks of further regionalization for Island schools recently came to a head after an organization conducted a study of the Island’s educational landscape and recommended a regional approach, the new superintendent, a regionalized role in itself, would be at the forefront of further conversations on the topic.
The leadership role also includes responsibility for one of the most high-stakes undertakings the school district has ever seen — an estimated $334 million renovation of the high school. The tax implications of the project for the local population will reverberate through the next 30 years, while a new building could positively serve generations of future learners.

As the search for a superintendent ramps up, there’s additionally an active search for a new principal of the Martha’s Vineyard Regional High School, following news that interim Principal Sean Mulvey will return to his role as a school counselor next fall.
The next community forums are scheduled as follows:
- Wednesday, Jan. 14 at 5 pm at the Martha’s Vineyard Regional High School (in-person only)
- Thursday, Jan. 15 at 7:30 pm on Zoom (link here)
There’s also an online survey, where residents can write in qualities they’re looking for in the next superintendent of schools, available at bit.ly/MVYPS_SuperintendentSurvey.


