At the age of software as a service (SasS) and cloud computing as compared to what is used to be earlier, designing product strategies is a challenging concern for software product management researchers. Comparative statics models are considered to identify software market characteristics while assessing the managerial decisions during the software product strategy design. However, their applicability in dynamic market analysis is rather limited. Important concerns in dynamic market such as dynamic pricing cannot be fully estimated. This motivated the development of a simulation-based dynamic model to evaluate the efficiency and effectiveness of using different pricing models. The proposed (simulation) approach given in details in this paper can be used in conducting complex analysis of software product strategy that involves consideration of product strategy as a portfolio of interrelated solutions rather than a set of independent managerial decisions.