A system for controlling a drive operation of a machine having a payload container. A controller is configured to determine a current payload disposed in the payload container based upon a load sensor and determine a number of completed material loading cycles of a work implement. The controller is further configured to determine an estimated number of material loading cycles required to load the payload container based upon a desired payload, the current payload, and the number of completed material loading cycles, and compare the number of completed material loading cycles to the estimated number of material loading cycles. After the number of completed material loading cycles is one or less than the estimated number of material loading cycles, a shifting operation may begin to shift the transmission into the drive gear.