Roslyn interim school Superintendent Gerry Dempsey’s office sits in the corner of the district’s central administration building, his computer in the corner near two sets of windows overlooking the back side of the adjacent Roslyn High School that allow light to extend past a conference table behind him.
Some of the faces he’s greeted each day since starting July 1 are familiar, enduring reminders of his brief tenure as interim superintendent in 2006-07, when he was tasked with leading Roslyn past an multimillion-dollar embezzlement scandal and regaining the trust of the school community.
But while paperwork and meetings haven’t changed much since then, Dempsey’s role has, to preparing Deputy Superintendent Allison Brown to take the reigns as his permanent successor in 2016-17.
“At this stage of my career,” said Dempsey, a Greenlawn resident, “I enjoy the opportunity to mentor and coach the next generation of school leaders.”
Dempsey succeeds former school Superintendent Dan Brenner, who resigned in January after accepting the same position with the Darien, Conn. school district, citing a shorter commute from his Westchester home as his primary reason for leaving.
Brown, Roslyn’s former assistant superintendent for curriculum and instruction, will split her oversight of the district’s academic programs with newcomer Michael Goldspiel.
“I’ve never seen anyone with more energy and enthusiasm for students and children of all ages, sizes, shapes, colors and creeds,” Board of Education President Meryl Waxman Ben-Levy said of Brown, the former East Hills Elementary School principal, in February. “You have not disappointed us in any one endeavor in anything you’ve taken on, and this is just another area where you will shine like the star you are.”
In his first few weeks, Dempsey has presided over the board’s annual reorganization meeting, and recently attended the board’s annual retreat to outline its mission for 2016-17.
He’s also learning how the job has changed, from the nuances of the state-mandated tax cap to New York’s teacher and principal evaluation system.
“Any time you come into a situation, you have to relearn the culture,” he said. “It’s different, there are different people in some cases and the circumstances are different, and there are plenty of changes to the culture of Roslyn. That’s really been my focus this summer, to relearn that culture.”
Dempsey has spent 47 years in public education, first as a teacher and then administrator and superintendent, having led the Farmingdale and Plainview-Old Bethpage school districts as well as each of Long Island’s BOCES centers.
In his second stint in Roslyn, and handling the implementation of the district’s $46 million capital plan, Dempsey said he plans to make Brown a significant part of his office’s decision-making process.
“I’ve been very impressed with Allison. She’s really wearing three hats, as elementary superintendent, deputy superintendent and almost superintendent,” he said.
In an emailed statement to the Roslyn Times in February, Brown said she is “excited and honored to have this incredible opportunity, and deeply grateful to the board of education for putting their trust in me.”
“The children and families of Roslyn have come to mean so much to me over the last few years, and I am looking forward to serving them in a new leadership role,” she said.
Dempsey also noted that because he previously served Roslyn alongside Ben-Levy, board Vice President Cliff Saffron and Trustee David Seinfeld, he understands the board’s mindset as “a place committed to excellence of academic program and meeting the needs of every student.”
“I know the consistency with their goals is still there,” he said. “I think of these leadership jobs as opportunities to make contributions to education, and it’s an honor to be considered and make that contribution.”
