Systems and methods including one or more processors and one or more non-transitory computer-readable media storing computing instructions that, when executed on the one or more processors, cause the one or more processors to perform functions comprising: determining at least one fleet delivery route for delivery of one or more items of one or more orders to one or more locations using a vehicle fleet; dynamically shuffling the at least one fleet delivery route by at least evaluating a cost differential; when the cost differential satisfies a threshold: removing the first order from the source route; inserting the first order into the first other delivery route; and communicating the first order to a first other deliverer associated with the first other delivery route. Additional embodiments are disclosed herein.