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Marblehead is preparing to replace its two most senior administrators within the same stretch of months, a convergence that arrives just as the town begins spending the largest tax increase its voters have ever approved.
Chief Financial Officer Aleesha Nunley Benjamin will leave in August to become chief financial officer for Nantucket, where she is scheduled to start in September, the town announced July 10. Her exit follows Town Administrator Thatcher W. Kezer III's decision to retire Dec. 31. The two spent the past year building and defending the financial plan behind Marblehead's override package, and both will be gone within roughly four months of one another.
Their overlapping departures create a straightforward tension for the town. Benjamin and Kezer were recruited into troubled operations and produced work valued enough that one is moving to a larger island finance job and the other is leaving on his own terms. But much of the forecasting, systems modernization and override strategy they advanced was closely identified with them personally, and both are leaving before that work is fully embedded.
Finance office short-staffed from the start
Benjamin arrived in 2023 to run a finance operation that had been without a permanent director for more than a year. The town recruited her for her municipal budgeting experience and financial-reporting background, and officials framed the hire as restoring stability to a central administrative post.
She inherited a department still dependent on paper-based processes. Kezer has described the town's information-technology systems as "on its last breath" when he arrived in June 2022, and the shift from paper to digital became a shared project across his and Benjamin's tenures.
Benjamin's most visible contribution was helping turn Marblehead's structural budget problem into a sustained public argument. Rather than presenting one year at a time, she and Kezer built multiyear forecasts showing a gap that widened each year without new revenue.
Those figures moved as assumptions were refined. A Finance Committee forecast in December identified a shortfall of roughly $6.8 million; by the Jan. 28 State of the Town, Kezer was presenting a fiscal 2027 gap of about $8.47 million. The growth was driven largely by health insurance. Benjamin told the Finance Committee she had applied a 15 percent projected increase to premiums — the low end of estimates that ran as high as 18 percent — based on guidance from the Group Insurance Commission. That single increase, she said, would consume nearly all of the $2.1 million the town gains annually in property tax revenue under Proposition 2½.
The forecasts pointed to a stark alternative. Balancing fiscal 2027 without new revenue, Benjamin said, would require eliminating more than 50 town-side positions, though she cautioned the real number could be higher because laid-off workers are owed unemployment pay. More than 184 workers are funded through the general fund, she said.
Building the case for an override
That analysis became the foundation of the override campaign. On June 9, voters approved a $15 million operating override and a $2,298,575 trash and recycling override, a combined $17.3 million increase to the tax levy. The operating measure passed 4,278-3,594, drawing 54.3 percent of the vote. The combined package ranks second in Massachusetts history among permanent Proposition 2½ increases, trailing only Brookline's $23.25 million.
In announcing Benjamin's departure, Kezer credited her with the numbers underneath that vote. She "played a critical role in developing the detailed financial analyses that supported our annual budgets and Proposition 2½ override planning," he said. The assessment is an outgoing administrator's appraisal of a departing colleague, and the override's passage cannot be attributed to any one official.
Benjamin was blunt in public about what the town had and had not been funding. "Exclusions have maintained the town's AAA bond rating," she told officials in October, referring to voter-approved debt for capital projects. "But we're not funding our operations and maintenance, and that's a serious issue."
Kezer's announcement credited Benjamin with leading the shift to electronic financial systems, improved budget monitoring and a reorganization drawing accounting, treasury, collections, assessing and IT into closer coordination. The town describes that reorganization as ongoing, not finished.
The record also shows how much she was carrying. As of March, Benjamin was serving as the town's sole IT administrator for 190-plus positions while simultaneously overseeing a migration to the Munis accounting system. "It's a lot of people wearing several hats," she told the Select Board. "I don't think it's sustainable."
The budget the board ultimately advanced, roughly $56.6 million, reflected a middle path Kezer called "Scenario B," pairing targeted cuts of about 18 positions with a curbside trash fee rather than the harsher option that would have eliminated roughly 56 positions, a 30 percent workforce reduction. Voters later converted that fee concept into the trash override.
Two exits, one transition
The simultaneity is the news. There is no evidence in the town's record that Benjamin left because Kezer is leaving; he has said he made his own decision before the override vote. But their exits pull two closely linked bodies of knowledge out of Town Hall at once — the forecasting models and override framework on one side, the administrative restructuring and search for continuity on the other.
Some of that work is now anchored in structures meant to outlast individuals. A memorandum of understanding among the Select Board, School Committee and Finance Committee commits the town to drawing down the override money on a set schedule. Kezer has cast the override itself as a reprieve rather than a permanent fix, warning that costs will keep climbing.
Other pieces appear more dependent on the people leaving: the Munis transition, the unfinished department reorganization and the forecasting judgment Benjamin exercised in public meetings.
The Select Board is already recruiting. Chair Dan Fox has said the board's immediate step is hiring an executive search firm, which he suggested selecting by late July or mid-August, giving Marblehead roughly six months to find someone before Kezer walks out the door. Benjamin's departure adds a second search on a faster clock; the town has said it will begin recruiting a chief financial officer immediately, with Benjamin assisting through August.
The board has discussed building in overlap between administrators and, if needed, bringing Kezer back for a stretch after the transition. Kezer is assembling what he called a "big book" laying out what the job entails for his successor. No comparable handoff document has been described publicly for the finance office.
Whoever fills the two posts will inherit the first full year of override spending, a bond rating the town wants to protect and a finance department Benjamin herself called stretched. The central question for Marblehead is not whether the reforms were sound but whether they were institutionalized deeply enough to survive the people who built them.Marblehead is preparing to replace its two most senior administrators within the same stretch of months, a convergence that arrives just as the town begins spending the largest tax increase its voters have ever approved.
Chief Financial Officer Aleesha Nunley Benjamin will leave in August to become chief financial officer for Nantucket, where she is scheduled to start in September, the town announced July 10. Her exit follows Town Administrator Thatcher W. Kezer III's decision to retire Dec. 31. The two spent the past year building and defending the financial plan behind Marblehead's override package, and both will be gone within roughly four months of one another.
Their overlapping departures create a straightforward tension for the town. Benjamin and Kezer were recruited into troubled operations and produced work valued enough that one is moving to a larger island finance job and the other is leaving on his own terms. But much of the forecasting, systems modernization and override strategy they advanced was closely identified with them personally, and both are leaving before that work is fully embedded.
Benjamin sounded a more personal note in a farewell message to town staff. "While I am excited for the next chapter of my career, leaving this community is far more difficult than I ever imagined," she wrote in a July 10 email to all town employees, calling the job "one of the greatest honors of my career." She framed the work in the same terms she had used in public budget meetings, telling staff that "every budget represents people" and that "every financial decision affects employees, residents, and the future of Marblehead." The override year, she wrote, "reminded me how much can be accomplished when people come together with professionalism, respect, and a shared commitment to doing what is best for Marblehead."
Finance office short-staffed from the start
Benjamin arrived in 2023 to run a finance operation that had been without a permanent director for more than a year. The town recruited her for her municipal budgeting experience and financial-reporting background, and officials framed the hire as restoring stability to a central administrative post.
She inherited a department still dependent on paper-based processes. Kezer has described the town's information-technology systems as "on its last breath" when he arrived in June 2022, and the shift from paper to digital became a shared project across his and Benjamin's tenures.
Benjamin's most visible contribution was helping turn Marblehead's structural budget problem into a sustained public argument. Rather than presenting one year at a time, she and Kezer built multiyear forecasts showing a gap that widened each year without new revenue.
Those figures moved as assumptions were refined. A Finance Committee forecast in December identified a shortfall of roughly $6.8 million; by the Jan. 28 State of the Town, Kezer was presenting a fiscal 2027 gap of about $8.47 million. The growth was driven largely by health insurance. Benjamin told the Finance Committee she had applied a 15 percent projected increase to premiums — the low end of estimates that ran as high as 18 percent — based on guidance from the Group Insurance Commission. That single increase, she said, would consume nearly all of the $2.1 million the town gains annually in property tax revenue under Proposition 2½.
The forecasts pointed to a stark alternative. Balancing fiscal 2027 without new revenue, Benjamin said, would require eliminating more than 50 town-side positions, though she cautioned the real number could be higher because laid-off workers are owed unemployment pay. More than 184 workers are funded through the general fund, she said.
Building the case for an override
That analysis became the foundation of the override campaign. On June 9, voters approved a $15 million operating override and a $2,298,575 trash and recycling override, a combined $17.3 million increase to the tax levy. The operating measure passed 4,278-3,594, drawing 54.3 percent of the vote. The combined package ranks second in Massachusetts history among permanent Proposition 2½ increases, trailing only Brookline's $23.25 million.
In announcing Benjamin's departure, Kezer credited her with the numbers underneath that vote. She "played a critical role in developing the detailed financial analyses that supported our annual budgets and Proposition 2½ override planning," he said. The assessment is an outgoing administrator's appraisal of a departing colleague, and the override's passage cannot be attributed to any one official.
Benjamin was blunt in public about what the town had and had not been funding. "Exclusions have maintained the town's AAA bond rating," she told officials in October, referring to voter-approved debt for capital projects. "But we're not funding our operations and maintenance, and that's a serious issue."
Kezer's announcement credited Benjamin with leading the shift to electronic financial systems, improved budget monitoring and a reorganization drawing accounting, treasury, collections, assessing and IT into closer coordination. The town describes that reorganization as ongoing, not finished.
The record also shows how much she was carrying. As of March, Benjamin was serving as the town's sole IT administrator for 190-plus positions while simultaneously overseeing a migration to the Munis accounting system. "It's a lot of people wearing several hats," she told the Select Board. "I don't think it's sustainable."
The budget the board ultimately advanced, roughly $56.6 million, reflected a middle path Kezer called "Scenario B," pairing targeted cuts of about 18 positions with a curbside trash fee rather than the harsher option that would have eliminated roughly 56 positions, a 30 percent workforce reduction. Voters later converted that fee concept into the trash override.
Two exits, one transition
The simultaneity is the news. There is no evidence in the town's record that Benjamin left because Kezer is leaving; he has said he made his own decision before the override vote. But their exits pull two closely linked bodies of knowledge out of Town Hall at once — the forecasting models and override framework on one side, the administrative restructuring and search for continuity on the other.
Some of that work is now anchored in structures meant to outlast individuals. A memorandum of understanding among the Select Board, School Committee and Finance Committee commits the town to drawing down the override money on a set schedule. Kezer has cast the override itself as a reprieve rather than a permanent fix, warning that costs will keep climbing.
Other pieces appear more dependent on the people leaving: the Munis transition, the unfinished department reorganization and the forecasting judgment Benjamin exercised in public meetings.
The Select Board is already recruiting. Chair Dan Fox has said the board's immediate step is hiring an executive search firm, which he suggested selecting by late July or mid-August, giving Marblehead roughly six months to find someone before Kezer walks out the door. Benjamin's departure adds a second search on a faster clock; the town has said it will begin recruiting a chief financial officer immediately, with Benjamin assisting through August.
The board has discussed building in overlap between administrators and, if needed, bringing Kezer back for a stretch after the transition. Kezer is assembling what he called a "big book" laying out what the job entails for his successor. No comparable handoff document has been described publicly for the finance office.
Whoever fills the two posts will inherit the first full year of override spending, a bond rating the town wants to protect and a finance department Benjamin herself called stretched. The central question for Marblehead is not whether the reforms were sound but whether they were institutionalized deeply enough to survive the people who built them.
