The chapter discusses the developed technology for managing the digital configuration of an organizational system, including cyber-physical systems, implemented as part of digital transformation. The technology consists of building a business model for the joint use of a digital balanced scorecard and a data envelopment analysis method. The digital balanced scorecard consists of a digital transformation strategic map and its complementary key success factors and key performance indicators. Within the framework of the described technology, it is proposed to use a two-stage scheme for the method of analyzing the operating environment, and its formal description is given. The possibility of modeling the configurations of the digital transformation strategy of an organizational system based on the use of a digital twin of the organizational system, implemented in the form of a simulation model, is described. A method for increasing the productivity of organizational systems through their digital transformation is proposed. The chapter proposes to select the configuration of the digital transformation of an organizational system by assessing each individual strategy based on real company data, as well as using forecast data obtained as a result of experiments with a simulation model. An algorithm for selecting the best configuration for the OS digital transformation strategy has been developed and described. The structural diagram of the organizational system digital transformation, including the double cycle of digital transformation, is described step by step.