The Board of Selectmen shall appoint a Town Manager who shall be the Chief Executive Officer of the Town to serve at the pleasure of the Board of Selectmen and who shall be chosen exclusively on the basis of his executive and administrative qualifications, character, education, training and experience. At the time of his appointment, said Manager need not be a resident of the Town of Winchester or of the State of Connecticut.
The compensation of the Town Manager shall be fixed by the Board of Selectmen and shall not be decreased except at the beginning of a fiscal year of the Town by a vote of the Board taken at least one (1) month prior to that date.
Repealed November 2, 2010.
The Town Manager shall devote his full time to the duties of his office and shall hold no other employment, without consent of the Board of Selectmen.
The Town Manager shall give the Board of Selectmen thirty (30) days advance notice upon the voluntary termination of his employment.
The Town Manager shall be removed, as herein provided, by at least five Selectmen each voting in the affirmative. The Board of Selectmen shall adopt a resolution stating its intention to remove the Town Manager at least thirty (30) days before the proposed removal. A copy of the resolution shall be served forthwith on the Town manager who may, within ten (10) days, demand a public hearing, in which event the Manager shall not be removed until such public hearing has been held. Upon the passage of such a resolution, the Board may suspend the Manager from duty, provided the salary of the Town Manager shall continue until the removal from office; and in the event of such removal the Town Manager shall be given termination pay equivalent to one (1) month's salary.
A. 
During the period of vacancy, suspension, or disability in excess of two (2) weeks, in the office of Town Manager, the Board shall appoint by resolution a person, other than a Selectman, as Acting Manager to have all the powers and duties of the Town Manager provided for herein, and to serve for a period not to exceed six (6) months.
B. 
The Town Manager may designate a department head as Acting Town Manager to serve as Town Manager, except in matters of appointments and removals, for a period not to exceed two (2) weeks, during the period of the Town Manager's temporary absence or disability. Appointments and removals shall be made by a majority of the Board of Selectmen acting in accordance with the provisions of this Charter.
C. 
In the event the Town Manager fails to make such designation the Board may by resolution appoint an Acting Town Manager to perform all the duties of Town Manager, except in matters of appointments or removal, for a period not to exceed six (6) months, during the period of the Town Manager's temporary absence or disability.
Whenever there shall be a vacancy in the office of Town Manager for any reason the Board of Selectmen shall appoint a Town Manager as successor within one hundred eighty (180) days after such vacancy occurs.
The Town Manager shall have the following duties, which the Board of Selectmen shall not diminish by ordinance, vote or otherwise, except those powers and duties imposed on him by the Board under the following provisions of this section:
A. 
Be directly responsible to the Board of Selectmen for the administration of all departments, agencies, offices and boards appointed by the Town Manager and shall supervise and direct the same;
B. 
See that all laws and ordinances governing the town are faithfully executed; make periodic reports to the Board and shall attend its meeting with full right of participation in its discussion, but without a right of vote;
C. 
Prepare and cause to be printed, as soon as possible after the close of the fiscal year, an annual town report;
D. 
Recommend to the Board such measures as he may deem necessary or expedient;
E. 
Keep the Board fully advised as to the financial condition of the Town;
F. 
Prepare and submit to the Board an annual budget; and
G. 
Exercise such other powers and perform such other duties as may be required of him by ordinance or resolution of the Board not inconsistent with this Charter.
The Town Manager shall appoint all department heads and other officers and employees of the Town except as otherwise specifically provided by this Charter and except employees in the offices of elected officials and Boards, and officers and Boards appointed by the Board of Selectmen. In lieu of any appointment by the Town Manager or any of his appointees to any office under his jurisdiction, the Town Manager may, subject to the approval of the Board, perform the duties of any office under his jurisdiction except those of the Town Treasurer and Finance Director, provided, in case the Town Treasurer is absent or unable to act, the Town Manager may countersign checks.
Neither the Board of Selectmen nor any of its committees or members shall dictate the appointment of any person to office or employment by the Manager, or in any manner interfere with the Manager or prevent him from exercising his own judgment in the appointment of officers and employees in the administrative service. Except for the purpose of investigation the Board of Selectmen and its members shall deal with the administrative service only through the Manager and neither the Board nor any members thereof shall give orders to any subordinate of the Manager, either publicly or privately.