Organizations are evolving at an ever-increasing rate due to economic changes, globalization, and technology enabled changes such as e-business. These changes require existing and new software systems to be flexible enough to support rapid change while still being reliable and cost effective. Software flexibility has previously been studied only from a structural perspective with little attention to the people and processes that support the software, especially in the maintenance environment where most changes occur. This research builds on a previously validated technology flexibility model with two dimensions: structural and process flexibility (Nelson and Ghods 1998). We empirically test the relationship of flexibility to the performance of the software system and the IS support team. The relationships between flexibility and performance are analyzed using a ìfitî analysis to fully understand the complexity of the relationships. Our findings indicate that software flexibility is related to both system and team performance, and is characterized by the amount of interaction, or ìfit,î between structural and process flexibility.