The D&RGW's flying herald was created by a secretary in the Rio Grande's Denver office in response to a 1939 contest. If I remember my history correctly, the contest was open only to employees.
Once adopted, the new herald was applied to equipment, structures, etc., as they were repainted. The first applications (499 was one, I believe) appeared to be hand-painted. In short order, stencils were made.
An interesting note, as applied to steam locomotive tenders, the "Rio Grande" was supposed to "lean" towards the front of the locomotive, thus the left side stencils were different than the right. I was told that the right side stencil was not available or was lost for a time in the 1950's, when 487 and 497 were shopped in Alamosa. Thus, the left side stencil was used on the right side of these, making the Rio Grande "fly" backwards on the right side of these two locomotives.
In the last years of Rio Grande operation of the Silverton Branch, the left side stencil was not used, so the right side stencil was used exclusively on the 470's during the late '70's.