The advances in IT-enabled Innovations have pushed enterprises to utilize their interrelated resources effectively and adopt suitable decisions on business development. Firms create more than the traditional value for customers, markets, and relationships in order to develop competitiveness within the long-term activity. Especially, customers have the most supplementary choices than ever to choose what they want nowadays. This paper applied the framework of Simulation-based Strategic Decision Support System (SSDSS) in order to investigate customer brand development through five stages from unaware to loyal customers. This newly developed Strategy Dynamics approach based on System Dynamics methodology that could enable managers to realize their internal obstacles, get insights of resource-driven performance to improve their future performance over time. By adopting real case study of a tea company in Taiwan, a numeric-based analysis through different scenarios demonstrates how the proposed SSDSS did help to formulate business development strategies for optimal performance. In addition, IT-enabled innovations in strategic thinking and decision making both could be the enabler for business performance. The anticipated outcome of this paper is the identification of the business transformation and growth that affect the sustainable development of the enterprise. As a result, the quality of decision-making could be enhanced and the model could be applied empirically in other related industries and internationally.