He was one of the pioneers of the trucking industry in Pennsylvania. Between 1938 and 1945 he operated his own company, Bockman Motor Express. In April 1943 he acquired C & M Motor Freight. C & M was run by R. A. Miller and R. J. Miller in Grove City, Pa. The company served point in northwestern Pennsylvania and the Ohio areas of Cleveland and Warren.

Two years later Bockman joined his business with Clyde Duffee to manage Duffee Motor Express. In 1956 Duffee was acquired by Erie-Pittsburgh Motor Express, Inc. Henry Bockman served as the Oil City, Pa terminal manager until his retirement in June 1967. Two years later, in June 1969, Erie-Pittsburgh was acquired by Mushroom Transportation Co. Inc.