He started out in junior hockey with the Kitchener Empires of the Ontario Hockey Association in 1932-33. Hiller went on to play more junior with the Sudbury Cub Wolves in the next two years and senior with the Sudbury Tigers and the Sudbury Falcons, winning the Allan Cup in 1935-36. After a year in Great Britain with the Harringay Greyhounds, Hiller was signed by the New York Rangers. He played one season for their farm team the New York Rovers and then joined the NHL team. He won the Stanley Cup in 1940.