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Many real-life combinatorial optimization problems are subject to a high degree of dynamism, while, simultaneously, a certain level of synchronization among agents and events is required. Thus, for instance, in ride-sharing operations, the arrival of vehicles at pick-up points needs to be synchronized with the times at which users reach these locations so that waiting times do not represent an issue. Likewise, in warehouse logistics, the availability of automated guided vehicles at an entry point needs to be synchronized with the arrival of new items to be stored. In many cases, as operational decisions are made, a series of interdependent events are scheduled for the future, thus making the synchronization task one that traditional optimization methods cannot handle easily. On the contrary, discrete-event simulation allows for processing a complex list of scheduled events in a natural way, although the optimization component is missing here. This paper discusses a hybrid approach in which a heuristic is driven by a list of discrete events and then extended into a biased-randomized algorithm. As the paper discusses in detail, the proposed hybrid approach allows us to efficiently tackle optimization problems with complex synchronization issues.