The fleet management system (FMS) plays a vital role in truck and shovel open-pit mining operations. The list of expectations from the FMS ranges from data recording to making operational decisions. This article proposes a nested fleet management system (N-FMS) for open-pit mining operations. The primary contribution of the proposed FMS is connecting the operation to the strategic plan by incorporating shovel allocation and plant feed optimization. Another contribution of the proposed N-FMS is that it simultaneously optimizes the utilization of the shovel fleet and truck fleet. The proposed FMS makes decisions using two nested multiple-objective mixed-integer linear goal programming models. Results of the implementation of the developed N-FMS in a metal mining case study show that compared to a locked-in operation, the mine experienced a 14.6% improvement in its required truck fleet capacity to meet the production target.