All positions subject to this bylaw shall be assigned to a classification. Each classification shall, in turn, be allocated to a pay grade. When a new position is proposed, the applicable department head shall file with the Town Administrator a written request for classification of that position. When a position has changed substantially as to the kind and/or level of work, the department head may file with the Town Administrator a request for (or, alternatively, the Town Administrator may initiate the process for) a classification change. In either event, the request shall be accompanied by a proposed job description for the position. The Town Administrator shall evaluate the position and shall make a decision concerning the appropriate classification of the position. The Town Administrator's decision shall be accompanied by documentation substantiating the decision and, with respect to reclassification requests, shall include an analysis of the changes to the position.