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When Christopher G. Senior became Winchester’s town manager in January, he made a habit of visiting departments instead of waiting for employees to come to him. One early stop was the Department of Public Works.
“I walked through the building, and people were like, ‘What are you doing here?’” Senior said in an interview this month. “I’m saying hello.”
He keeps standing meetings with finance and planning staff, board chairs and school leaders.
He describes the manager as “a catalyst” and “the support mechanism,” someone who works “like a conductor” to “harmonize the work that’s being done.”
Eight months after he was sworn in Jan. 14, much of his agenda remains in development, according to Senior and the public record.
A performance dashboard is unfinished. A plan to put all permitting on one electronic platform has not reached Town Meeting. The structural budget gap that preceded him persists.
The fiscal backdrop
Senior, who spent 12 years as Cohasset’s town manager, was hired after two other finalists withdrew in December 2025. His $171.7 million fiscal year 2027 plan, submitted Feb. 15, was built against projected operating deficits of $3 million to $5 million in coming years.
The Select Board set an $11.5 million Proposition 2½ override, which voters rejected March 21, in a 2,558-2,265 vote. Town Meeting adopted a one-year “bridge budget” that cut 32.5 school positions and froze town hiring.
Senior credited the chairs of the Finance Committee, School Committee and Select Board with shaping it.
Moody’s affirmed Winchester’s Aaa bond rating June 15. Senior said keeping it requires active management.
Officials reported about $21 million in free cash, roughly $10 million of it treated as a floor to protect borrowing capacity.
“The turn has taken place,” he said. “We’re starting to draw down reserves.”
He frames the central problem as a gap between revenue growth and cost growth, citing diesel fuel, asphalt, tariffs and employee pay. Proposition 2½ limits annual growth in the property tax levy to 2.5%, plus new construction, unless voters approve an override.
“You can’t match inflation,” he said.
Still, he said the law “does force some very hard reckonings, and that was the purpose of the law.”
“I do think the state needs to give localities more local options,” Senior said, pointing to proposals such as a higher cap on the local meals tax.
The board also asked Senior to take a fresh look at capital planning, with more than $100 million in needs identified over five years. He said his recommendations were tested internally before going to the committee that reviews capital requests.
“It wasn’t my personal recommendations,” he said. “We worked with staff.”
Structure, permits and data
Senior said Winchester’s organization was “a little bit more siloed” than he expected.
“Everyone’s doing their good work, but they were doing it kind of parallel, not so much in harmony,” he said.
He said departments have long run joint programs and he is not suggesting employees don’t talk. His concern is that services cross departmental lines.
“They’re not seeking a building permit or a board of health permit or a planning permit. They want to open a restaurant,” he said, of applicants.
Winchester uses OpenGov for building and zoning permits, but Planning Board applications are filed on paper, Senior said. He intends to ask the fall Town Meeting, which convenes Nov. 5, to fund moving every permitting office onto the platform so applications move electronically between departments.
The departments support it, he said, though it will cost more than the current arrangement.
“I can’t tell you we’re going to save this many dollars, but we’re going to be a lot more effective,” he said. “And it’s going to save time and hours.”
Senior has said more than 20 employees report directly to him. He has not announced a reorganization in Winchester, but he has encouraged the library, Recreation Department and elder services staff to meet regularly on their own.
Senior talked about data-driven decisions while interviewing for the job. In North Hempstead, N.Y., a town of about 200,000 people, he helped build a 311 line and a performance system called TownStat, modeled on Baltimore’s CitiStat, that tracked work such as pothole repairs.
“Every community is different,” he said. “You can look at what’s being done effectively somewhere else and say, ‘Hey, can I adapt that to my use?’”
In Winchester, he said, he found information that exists but is hard to view townwide. Each department has its own properly procured copier contract, leaving no central picture of printing costs. Leave is recorded for payroll, but not in a form that can be analyzed across departments, and the town still uses paper timesheets.
“I’m not criticizing anybody,” he said.
The dashboard, on his goal list since winter, is not as far along as he wants, he acknowledged, and for now would be built in spreadsheets. He said he plans to redefine a position in his office left open by a retirement toward budget and performance work and hopes to begin sharing data, such as police and fire call volumes, this fall.
“I’m 100% a believer in this stuff,” he said. “It turned out some of the stuff that I thought would be fairly easy is not.”
Evaluation and renewal
The board adopted goals for Senior on March 2 covering board support, staff leadership and financial management.
His first formal evaluation returned overall category ratings above the “satisfactory” mark his contract requires. It credited him with learning the organization quickly and supporting staff; members also asked for stronger follow-through, clearer recommendations and more comprehensive written analysis.
“I didn’t take it as criticism,” Senior said. “It’s development. It’s like, ‘Hey, you’re doing this well. We need you to do this better.’”
At a Sept. 14 goal-setting discussion, Select Board member Michelle Prior said the dashboard needs “to get more than just a draft, but actually done” and asked for recommendations that are “a little more written and a little less verbal.”
His contract, signed Jan. 9, set a term through Dec. 31, 2026, with a one-year renewal option tied to an evaluation completed by Sept. 30.
On Aug. 10, Vice Chair William McGonigle moved to renew, citing the scores. No one seconded. Prior wanted Senior’s February goals, self-assessment and proposed new goals first and said her position on renewal had not changed.
“That’s a shift, and it’s outside the contract,” McGonigle said.
Select Board Chair Anthea Brady said the contract ties renewal to the evaluation, not future goals. Michael Bettencourt said members were asking for two weeks, not months. Senior interjected, “Can I take the temperature down a few degrees, please?”
On Aug. 24, the board, down to four members after Paras Bhayani’s July resignation, renewed Senior 4-0 through Dec. 31, 2027, raising his salary by $5,750, or 2.5%, to $235,750. Brady said she would bring a “more formalized list” of 2027 goals Sept. 28.
Last winter, a resident complained about snow clearing. Public works staff told Senior the area had since been cleared, but had been missed after an earlier storm.
“If we don’t do something, we can’t pretend we did,” he said when asked whether residents had raised complaints that showed the town needed to do better. “You can’t tell people that the sun is shining when it’s pouring rain.”
Will Dowd is a Massachusetts journalist who covers municipal government and community life for Winchester News. He is also the founder and editor of The Marblehead Independent, a reader-funded digital newsroom.
