Hebe began his career as a salesman for America LaFrance in Elmira, New York, in 1971. He was promoted to Regional Sales Manager in 1974. In 1976, Hebe joined the Kenworth Corporation as Dealer Development Manager in Kansas City and was named General Manager in 1977. In 1978, he became General Manager of Kenworth Factory Branch in Kansas City and later that year became Owner and General Manager of Kenworth in Tampa. In 1984 he was promoted to National Sales Manager and in 1987 to Assistant General Manager/Sales and Marketing of Kenworth in Seattle. In 1989, Hebe joined Freightliner Corporation as Senior Vice President of Sales and Marketing. In 1991, he was named Executive Vice President and assumed his present position as President and Chief Executive Officer in 1992.