In the digital economy conditions, further growth in the competitiveness of Russian enterprises depends on the success of their digital business transformation, without that the transition to a qualitatively different path of development is impossible. The purpose of the study is to identify organizational, economic, and digital business transformation problems of Russian enterprises and ways to solve them in the context of the transition to a digital economy. Research objectives: objective conditions analysis for digital transformation; control system diagnostic analysis, including the level of management processes automation; analysis of the organizational structure of Administration/Management, the companies personnel involvement degree, and the level of business processes development; analyze organizational culture and its capacity for digital transformation. The results obtained indicate that the most important obstacles to digital business transformation are: misunderstanding of the digitalization purpose, lack of competencies and knowledge, the internal resistance of employees and fear of change, lack of strategy, and lack of qualified specialists. To solve this problem, it is necessary to reconsider the vision of the company, consider the overall system, define targets, and present an example of the digital economy: organizational culture of the organization, organizational management structure, and business processes. In studies from the systems observation standpoint diagnostic analysis procedures, expert-analytical methods, methods for setting up a structural management system, procedures for functional and cost analysis, business process reengineering, building an organizational culture profile — Organizational culture assessment tool, guidelines for determining transformation figures in Russian enterprises. The research methodology also includes observation, conducting surveys, and interviewing experts.