A system and method according to which data associated with a plurality of trade requests is received, and an optimization network is generated, the optimization network including a plurality of nodes corresponding to the trade requests. The nodes are ranked in accordance with at least one business objective, and one or more of the requests are fulfilled in an order based on the ranking of the nodes. To fulfill the one or more requests, a solution is generated, the solution complying with one or more predetermined rules. In an exemplary embodiment, each of the trade requests corresponds to a request to trade a work assignment. In an exemplary embodiment, each trade request is a request by an airline crew member to trade an airline flight sequence, and the at least one business objective is based on airline crew member seniority.