Information Systems (IS) have come to play a larger role in how organizations function, including consideration in strategic planning. Responding to competitive change or enacting a new strategy often requires modifying or enhancing an organization’s IS. In this paper, the authors develop a process model of evolutionary change to address the role that IS plays in organizational strategy. The model is based in part on Miles’ strategic typology of Defenders, Prospectors and Analyzers. The model examines how strategic approaches influence attention to environmental change, investments in IS capabilities, and evolution of information systems. The behavior observed in the simulations corresponds with the theoretical hypothesis developed from the model. The conservative defender organization experienced few discontinuous changes in the simulated 20 years. The innovative prospector organization exhibited extensive change, while the balanced approach of the analyzer organization fell between the two extremes. This study has taken steps to create simulations that approximate the behaviors predicted by a theoretical process model. The success of the simulation modeling in this study builds a foundation for future research.