[2] He also spent a dozen summers as an employee of the Massachusetts Highway Commission, starting as a rodman and rising to the position of resident engineer.
[4] He was seen as the eventual successor to first deputy William D. Hawley, who was the chief advisor to the House and Senate committees on Ways and Means.
[8] In this role, Raymond oversaw the budget of every state department and had the ability to cut any expenditures he believed were unnecessary, which resulted in many new positions, projects, and buildings being canceled.
[10] He continued the pay as you go policy adopted by his predecessor, Robert A. Perkins, and in 1948, due in large part to contributions made by Raymond, Melrose became the first debt-free municipality in Massachusetts.
[11][12] In 1947, Governor Robert F. Bradford appointed Raymond to chair a commission tasked with studying fiscal relations between the state and municipalities and to look into potential sources of revenue.