After receiving his B.A. degree from the University of Minnesota, Robert Gaylord worked for companies in Minneapolis and Rockford, Illinois. In 1915 he married Mildred Ingersoll, a girl he had met while working in Rockford. Then in 1917 he went back to Rockford as vice president at Ingersoll Milling. He became president of the company in 1928, a post he held for 40 years. He made lasting changes in the methods of operations. One was his requirement that management justify the replacement of machines less than ten years old, and justify the retention of machines over ten years old. Under his leadership the company pioneered transfer machines for automobile powertrain components, and developed machines for battleship armor plate and tank hull construction. In 1968, he turned the CEO post over to his son, Edson, but continued as chairman.