In our paper, we focus on the characteristics of the organizational transformation process that integrates the product and the service paradigm to achieve a Product-Service System (PSS). Due to the outcome of our own research activities and recent literature about the servitization of manufacturing, the transformation towards PSS is considered as an organizational learning and renewal process that has special demands for collective learning and knowledge-sharing activities. These demands are regarded as particularly crucial to manage the integration of the product and service paradigm. For the design of a specific learning scenario that prepares individuals for the demands of PSS work environments and the challenges along this organizational development process, we refer to the 4I Framework of organizational learning as a conceptual background to frame the transformation towards PSS within a context-rich learning environment. The design of the PSS-related learning scenario addresses the challenges of the organizational transformation process towards PSS on the individual, group and organizational level. The role of participants as individual actors in this learning scenario is determined by a PSS-specific 4I Framework as a holistic approach in which learners have to work out strategies to overcome typical barriers of a PSS-related organizational transformation process. The PSS- related learning environment builds on a business game scenario which provides us with the opportunity to address the ambiguity and the dynamic character of the transformation process towards PSS. Furthermore, we outline the advantages of a game-oriented community approach that supports individual learners to understand how to integrate the product and the service paradigm collectively in a fictitious but reality analogous organizational environment.