J.E. Henry began his career in 1911 as a bookkeeper for a small bank in Indiana. His first job in the automotive industry was as branch manager for the Service Motor Truck Co. of Wabash, Indiana in their Kansas City office, a position he held for two years. He would later become the Secretary-Treasurer of the Philadelphia branch of the Lexington Motor Company.

In 1925, Henry became General Manager for the Buick Retail Co., in Jenkintown, Pennsylvania, where he remained for 10 years. He would resign from this position in 1935 to become the Regional Manager of General Motors for three years. In 1938, Henry purchased the Wilkie Buick Co., then the largest retail automotive dealer in Philadelphia, Pennsylvania, which he owned until his retirement in 1949.

After his retirement, Henry served as a Trustee and Chairman of the Building Committee for the American Oncologic Hospital in Philadelphia, and was also named an honorary President and Life Director of the Automotive Old Timers (now the Automotive Hall of Fame).