The Town Manager’s Office

Christopher Senior

When a culvert fails or a budget gap opens, the person with the most operational control in Winchester is an appointed professional, not an elected official. Christopher Senior is the Town Manager, hired by the elected Select Board to run the town day to day. He took the oath of office on January 14, 2026, in the Select Board Room at Town Hall, closing a transition that began when the previous manager resigned the summer before; two interim managers kept the office running while the board searched, and the board voted in December 2025 to offer Senior the job. He came to Winchester after twelve years as town manager of Cohasset. His contract runs two years with a salary of $230,000, a performance review due between nine and twelve months in, and a second year that depends on a successful evaluation by a majority of the board. That structure is the accountability lever: the manager answers to the five people the voters elected.

The charter, first adopted in 1975, defines the job. The Town Manager is responsible for the day-to-day operations of the town, appoints department heads and employees not serving directly under elected boards, enforces state law, town bylaws, and the charter, and prepares and administers the town’s annual budget. That last power is the big one. The budget Senior builds goes first to the Select Board and the Finance Committee, then to the 192 elected members of Town Meeting, who vote it line by line; in spring 2026 that meant a general fund budget of about $171 million. The split is deliberate: elected bodies decide what the town does, and the manager decides how it gets done. So when a resident wants a problem fixed, the plan usually crosses the manager’s desk first, then goes to the board for policy and to Town Meeting for money. Knowing which of those three doors your issue belongs to is most of the game.