Beginning as a metal fitter, he rose to the rank of chief engineer, contributing to the design of all Douglas airliners from the DC-1 to the DC-8.
Raymond is best known as the lead designer of the DC-3, "The Plane That Changed the World," the first airliner that could break even hauling passengers without a government subsidy and without carrying mail.
When Boeing and other aerospace firms proposed in the late 1960s to build a supersonic airliner with substantial subsidies from the US government, Raymond argued that the plane was not commercially viable.
The USA government ceased subsidizing the design of the American supersonic transport in 1971, whereupon it died.
At the end of World War II, Raymond proposed to the USAF that they create an organization to think about intercontinental warfare.