Where a lot of IT executives think of their careers as a game of checkers, planning one move at a time, Asiff Hirji has thought about his career as a game of chess, planning several moves in advance. He was an engineer by training, and realized he needed a more formal business education, so he got an MBA. He was a CIO multiple times over, most prominently at T.D. Ameritrade, but each time, he took on responsibilities beyond that role, eventually becoming president and COO of T.D. Ameritrade.