Customer specific value creation is an adequate mean for technology oriented small and medium sized enterprises (SMEs) to differentiate themselves in the global market place. To achieve this, a tradeoff between efficiency and individualization in value creation has to be handled. In context of mass customization, sales configurators help to accomplish this. However, implementing such solutions rise both an organizational and strategic challenge. Therefore, referencing the context of change management, configurator implementation project case studies and a cross-case analysis are presented. Based on this, a model of implementation phases is derived which allows for addressing the specific challenges and recommendations with respect to such projects..