The Plympton Board of Selectmen voted 2-1 on July 14 to offer the permanent town administrator position to interim administrator Robert Fennessy Jr., over the preference of Chair Nathaniel Sides, who argued the town’s looming budget pressures called for a candidate with a deeper municipal-finance background. Selectmen Dana Smith and Daniel Cadogan carried the motion, citing Fennessy’s experience running neighboring South Shore towns and his three months already on the job in Plympton.
The decision capped a two-meeting process that began July 9, when the board interviewed four finalists forwarded by a seven-member screening committee working with the consulting firm Community Paradigm Associates. Community Paradigm’s Bernie Lynch told the board the committee had winnowed roughly 30 applicants down to the four who appeared in public.
Fennessy has served as Plympton’s interim town administrator since late April, stepping in after Liz Dennehy — the town’s first-ever administrator — departed for Easton. An attorney of more than two decades and an adjunct professor at UMass Law School, Fennessy told the board he has held the administrator’s job, on either an interim or permanent basis, in Boylston, Kingston, Carver and Halifax, and served last year as interim human resources director in Brockton. He pitched himself as a package deal. “You’re not just getting a town administrator,” he said. “You’re getting an attorney,” an HR director, and “the only person who’s worn the town administrator shoes” in nearly all of Plympton’s neighboring communities. Asked what he saw as the town’s biggest challenge, he answered without hesitation: “Obviously, it’s financial.”
The other three finalists brought contrasting profiles. Christine DeMoranville, the Treasurer-Collector for the City of Taunton since 2022 and a 30-year veteran of banking and government finance, leaned on her investment and procurement record; she told the board Taunton had posted among the highest municipal investment earnings in the state on her watch and that she had earned her Massachusetts procurement (MCPPO) certification in March. Heather Hamilton, a former chair of the Brookline Select Board with a background at MassDOT and a municipal engineering firm, emphasized capital planning, grant strategy and communication, and said Plympton’s rural character and its prior female administrator had drawn her to the role. Sydney Viveiros, currently assistant town accountant in Lakeville and previously executive administrative assistant to the Acushnet town administrator, presented herself as a hands-on, budget-conscious generalist steeped in day-to-day municipal operations, and repeatedly likened Plympton to Acushnet.
Sides opened the July 9 session with a warning to the audience that the finalists were sitting for genuine job interviews and deserved courtesy. Each candidate fielded questions on their first 100 days, HR and collective bargaining, grants and procurement, economic development in a town with almost no commercial tax base, and their working relationship with a three-member board. Sides also closed each interview with the same offbeat prompt — “You’re a tree. What kind of a tree are you and why?” DeMoranville and Fennessy both chose the oak; Hamilton picked a willow; Viveiros, a Japanese maple.
When the board reconvened July 14 to deliberate in open session — a requirement under the state’s open meeting law — all three members went out of their way to praise the field. “I wish we had more jobs that we could hire all four of them for,” Cadogan said, calling every finalist a strong fit for the town in some capacity. But the members diverged on who should get this job.
Sides made the case for DeMoranville. “The biggest issues that are facing the town for the next five years or so are financial in nature,” he said, describing her as a proven financial manager with procurement, labor and roughly four to five years of municipal experience. He stressed the choice was “certainly nothing against Bob,” whom he called “a wonderful choice, a safe choice.” Smith backed Fennessy, pointing to his record in contiguous towns and the fiscal strain facing Plympton and the wider South Shore: “We need somebody with more experience on the ground, having worked in other towns.” Cadogan also backed Fennessy on the strength of his interim tenure and resume, while sharply criticizing the process itself. “I vehemently disagree with the open meeting law that makes us criticize people in public,” he said, declining to rank the other candidates and calling the public deliberation “a disgusting process that the state makes us do.”
Cadogan ultimately moved to offer the position to Fennessy. Sides added the standard contingency that any offer be subject to successful contract negotiation, and the motion carried on a roll call: Cadogan and Smith in favor, Sides opposed, a reflection of the finance-versus-experience split rather than any objection to Fennessy.
Fennessy accepted graciously. “I’m truly honored by your vote today, even though it wasn’t unanimous,” he told the board. “It’s been a privilege serving as interim town administrator here. I learned a lot in a short amount of time, and there’s a lot more to learn.” He pledged an open-door policy, “always have, for 20 years.”
The financial anxieties that shaped the vote were on plain display earlier in the same July 14 meeting. Before taking up the administrator question, the board reviewed the town accountant’s year-end internal budget transfers for fiscal 2026, which totaled roughly $317,000 in departmental deficits. Sides singled out the police department, which had run about $128,000 — roughly 10 percent — over budget. “Given the current fiscal state of the town, we need to know every step of the way,” he said, pressing for earlier notice when accounts head toward deficit. The board approved the transfers unanimously, pending Finance Committee sign-off on reserve-fund pieces expected later that evening.
That strain traces back to the town’s most recent town meeting, where — as board members recounted during the interviews — Plympton drew roughly $800,000 from stabilization to close its budget gap and avoid a Proposition 2½ override. Members told candidates repeatedly that the maneuver was a one-time fix: stabilization is now largely depleted, the town has no current five-year capital plan, a proposed new fire station failed at town meeting, and an aging population worried about affordability sits alongside an influx of younger residents. Whoever holds the administrator’s chair, Sides said, will need “creative ways to increase revenue” heading into what the board described as one of its toughest budget years.