Tripod, an integrated bi-level transportation management system, is a smartphone application from the potential user’s point of view which would be instantly accessed prior to performing the trip. Since there are constantly several alternatives for any trip, Tripod considers a series and combination of various parameters, including departure time, mode and route, and rewards for each alternative with a number of redeemable points for goods and services called “Tokens”. The framework responsible for computing the optimized number of tokens awarded to the set of available alternatives in order to minimize the system-wide energy consumption under a constrained Token budget, is the System Optimization (SO) implemented in Tripod. To do so, a higher number of tokens would be awarded to the alternatives, guaranteeing a larger energy saving, less energy consumption, alternatively. SO is multimodal whereby public transit, private car, carpooling, etc. are being considered as the potential travel modes. Furthermore, SO is dynamic, predictive and personalized: the same alternative is rewarded differently, depending on the current and predicted future condition of the network and on the individual’s profile. In order to solve this problem, a multimodal simulation-based optimization model will be elaborated.