Generating an optimized pricing plan includes accessing a hierarchy comprising a sequence of levels, where each level includes an objective function and a set of constraints associated with the objective function. A mathematical programming model representing a pricing plan problem is determined for an item group comprising items. The following is repeated for each level of the sequence of levels: selecting a level comprising an objective function and a set of constraints associated with the objective function, determining an optimized boundary for the objective function, and adding a constraint generated from the optimized boundary to the set of constraints of a next level. An objective function of a last level of the sequence is optimized subject to the set of constraints associated with the objective function to yield an optimized result. An optimized pricing plan is generated in accordance with the optimized result.