MARBLEHEAD — Marblehead is entering a period of leadership transition as town officials begin the search for a new town administrator while also preparing to replace the town’s chief financial officer.

Less than a month after Town Administrator Thatcher W. Kezer III announced he would retire Dec. 31, Kezer announced Friday that Chief Financial Officer Aleesha Benjamin will leave Marblehead in August after accepting the chief financial officer position with the Town of Nantucket.

The departures come as town officials begin implementing the financial plan supported by the $15 million Proposition 2½ operational override approved by voters in June. Benjamin and Kezer worked together throughout the past year as Marblehead addressed a projected $7.7 million structural budget deficit, developed a long-term financial plan, and presented the override proposal to residents.

The Select Board has already begun the process of finding Kezer’s successor.

During Wednesday’s meeting, Select Board Chair Dan Fox said the board hopes to hire a new town administrator by October, allowing time for a transition before Kezer retires at the end of the year.

“If we’re looking to have a new administrator by year-end, likely someone is going to have to give a couple months’ notice,” Fox said. “So we’re looking, in theory, to hopefully end this process or hire someone by October.”

Fox said the board’s immediate priority is obtaining quotes from firms that specialize in municipal executive searches.

“Our first step is to really start to look for quotes for services, someone to hire to help us with the search,” Fox said. “I think that’s really our first step here, is to bring them in and to work with them.”

After selecting a search consultant, Fox said the board will determine whether to establish an interview committee to assist with the hiring process.

“I don’t think we have to decide that tonight,” Fox said. “I think we can discuss that next.”

Kezer said hiring a search consultant will not require a formal request for proposals because the anticipated cost is expected to be about $15,000, below the state’s procurement threshold.

“It’s under $50,000. It’s going to be about $15,000,” Kezer said. “So it’s just seeking quotes. It’s an administrative process.”

The town’s procurement office will solicit quotes before the Select Board selects a search consultant.

Fox described the timeline as preliminary and subject to change once a consultant is selected.

“This is a very general timeline,” he said. “I think probably some of these changes on the timeline once we decide who we want to use.”

Select Board member Jim Zisson said he had initially believed the process had already begun.

“I thought it had already been started, but that’s fine,” Zisson said.

No formal vote was required because seeking quotes is considered an administrative function.

Friday’s announcement means the town will also begin searching for Benjamin’s successor.

Benjamin joined Marblehead during a period of extensive financial planning and budget development. During her tenure, she worked on the town’s annual budgets, financial analyses, and long-range planning, including the financial modeling used throughout the Proposition 2½ override process.

In announcing her departure, Kezer credited Benjamin with helping guide those efforts.

“Aleesha Benjamin has been an exceptional member of our leadership team, and while we are saddened to see her leave Marblehead, we are excited for her as she begins this next chapter as Chief Financial Officer for the Town of Nantucket,” Kezer said.

He said Benjamin “played a critical role in developing the detailed financial analyses that supported our annual budgets and Proposition 2½ override planning, ensuring that our decisions were based on sound data, careful forecasting, and complete transparency.”

Kezer also credited Benjamin with leading the town’s transition from paper-based financial operations to electronic financial systems, improving budget monitoring, financial reporting, and long-range financial projections. He said her work included financial forecasting and strategic planning, helping Marblehead maintain its AAA bond rating and overseeing the ongoing reorganization of the Finance Department.

Calling Benjamin “a trusted advisor, an innovative leader, and a valued colleague,” Kezer said she “leaves Marblehead in a far stronger financial position than when she arrived.”

Benjamin will continue working with town leadership through August to help transition her responsibilities before joining Nantucket in September. The town said it will immediately begin recruiting its next chief financial officer.

Kezer, who has served as town administrator since June 2022, will remain in his position through Dec. 31 while assisting with the transition to his successor. His retirement will mark Marblehead’s fifth town administrator transition since 2018, following the tenures of John McGinn, Jason Silva, McGinn’s interim return, and Kezer.