Fleishman aims to bring passion and experience to Wayland’s schools. And some stability.

And it didn’t take long for David Fleishman to realize how much he missed his role leading a school system

“I find that you don’t always realize how much you enjoy a role until you leave it,” Fleishman says. “I missed the passion for working with students, and parents, and the faculty.”

Fleishman, who served as superintendent in Wayland for just over a year on an interim basis, was recently appointed as the permanent school superintendent of Wayland public schools.

Having served for almost 12 years as the superintendent of the much larger public school system in nearby Newton, Fleishman briefly left the world of K-12 school leadership in 2022 to serve as CEO of JVS Boston, a nonprofit workforce development and training organization.

But the pull of addressing the challenges of a school system proved irresistible to Fleishman.

“When I came as an interim in Wayland, I wasn’t sure at first that I wanted the permanent superintendent job,” he says. “But this is an opportunity to build. To build a team, to hire a lot of new people, including a mostly new central office. And there’s a rich history here [in Wayland] of really strong schools and community support. A rich tradition of excellence and quality.”

Tumultuous years

Recent years at the top of Wayland schools have been tumultuous, putting severe strains on that tradition. Fleishman’s immediate predecessor, Omar Easy, is still embroiled in his lawsuit against the Wayland schools alleging discrimination. Hired in July 2021, Easy was placed on administrative leave by the School Committee, just 19 months later, in February 2023.

The School Committee itself has completely changed over since Easy’ hiring during the throes of the pandemic in 2021 with all five current members having assumed office since 2023. 

Prior to Easy, Wayland’s schools were managed by superintendents with terms of five years (Paul Stein) and four years (Arthur Unobskey).

The instability, combined with the unprecedented challenges of the pandemic, deeply affected Wayland’s schools, shaking the confidence of parents, educators, and the broader community. The leadership and educational direction of the school system were called into question. Broader economic and social convulsions posed existential threats to many of the nation’s public-school systems–including Wayland’s vaunted schools, and their financial stability.

Wayland’s school leadership is aware of these challenges, and didn’t exactly drag out the process of finding a new superintendent

Choosing a new leader

“Originally, when we were looking for an acting superintendent, we wanted someone with a lot of experience stabilizing a district,” said Erin Gibbons, School Committee chair. 

By the time they were ready to start the search for a permanent superintendent, “it seemed like (Fleishman) had all the qualifications,” Gibbons said.

“We wanted someone with experience running a high-performing district, not someone who had been in an assistant role, but someone who had the title and the responsibility of being the one to run a high-performing district. (Fleishman) was a natural choice.

Gibbons pointed out that Fleishman has hardly been coasting in the interim role over the past 18 months. She pointed to the newly invigorated leadership of the special education team in Wayland as a sign of Fleishman hitting the ground running and taking the reins quickly, with the appointment of Ronnie Kessler as the new director of student services

“(Fleishman) really has the ability to build trust and relationships,” Gibbons said. “He was really able to get our staff and administration back onto the right track. Even in that time of acting and interim leadership, he was really able to move the district forward.”

Moving in the right direction 

Fleishman is the first to admit that Wayland is only now emerging from a “tough time” in the school system, and that many challenges still remain.

“Wayland went through a challenging time,” Fleishman said, coping with and slowly recovering from both the COVID-19 pandemic and the aftermath of the Easy tenure. 

“When you have a lot of leadership turnover, that’s tough for organizations, even the best organixati0ons, And the challenges here were not just in the superintendent’s office, but at the levels of many of the buildings. It was a tense time when I got here, but we’re working on culture and making the needed adjustments, and people think were moving in the right direction.”

In fact, a School Committee survey earlier in the fall fund that 69% of residents overall, and 77% of staff, give Wayland schools that coveted “headed in the right direction” response.

Just as significantly for Fleishman’s future in Wayland at least, many residents, school parents and non-parents alike, contacted the School Committee personally to say that they wanted to keep Fleishman around.

Good vibes like that led the school board members to hire Fleishman on a permanent basis last month, signing him to a four-year contract.

“We feel like with (Fleishman) on board on a permanent basis, we have laid the groundwork for getting back to the important work of continuing the tradition of excellent schools In Wayland,” Gibbons said.

“Now it’s time for the hard work of doing that work.”