Abstract: Example systems and methods of assigning shipping orders to delivery vehicles are presented. In one example, a delivery region may be segmented into delivery blocks. A shipping order density may be determined for each of the delivery blocks. Adjacent delivery blocks having corresponding shipping order densities may be merged to yield delivery areas. A cost of using each type of available delivery vehicle to transport a delivery job may be determined relative to a cargo capacity of the vehicle type, a delivery distance, and a shipping order density. Each of the delivery areas may be partitioned into delivery jobs based on the cost of using each of the vehicle types. Each of the delivery jobs may be assigned to one of the available delivery vehicles based on minimizing a total cost of using the vehicles to transport the delivery jobs.