The paper explores the issues of digitalization of the industrial complex and industrial markets in the context of the information network paradigm. The author presents an approach to assessing the process of the industrial complex transformation under deep penetration of digital technologies to the material sector of economy. We formulate the theoretical research platform based on the four approaches – neo-industrial, transaction, networking and marketing. The research findings show that industrial markets’ digitalization is integrated into the overall process of digital transformation of the industry, which consists of five consecutive stages – from the primary information and communication digitalization and to the industrial Internet. The author pays special attention to digitalization of producer-customer relationships in industrial markets on the basis of discrete-event and agent methods. The results of the empirical research pertain to the sectoral and regional characteristics of the digitalization of industrial markets in Russia. The author looks at nine enlarged industrial markets, identifies the distinctive features of their digital transformation and demonstrates a significant differentiation of industrial markets by both the level of the primary digitalization and the level of digitalization of relationships with suppliers and customers. We prove that the degree to which high technologies are applied by manufacturing sectors is dependent primarily on the level of digitalization, automation and networkization. When it comes to regional disproportions of industrial markets’ digitalization, the author concludes that the poor development of certain regions is due to their historical background and confirms the hypothesis that the concentration of high technologies influences the development of the regional digital society.