Due to the widespread introduction of a risk-based approach to doing business, effective organization and control of risk management digitalization processes is of great scientific and practical importance. One of the priority tasks is the search for effective digital risk management tools, their evaluation and optimization of choice. The purpose of the article is to study the issues of transformation of risk management tools and to develop methodology for assessing the feasibility of implementing risk management software at enterprises. The study used methods of system, factor and comparative analysis; structural, historical and logical approaches; methods of expert assessments, modeling. The article clarifies the concept of "digitalization of risk management", identifies key approaches to the digital transformation of risk management, identifies its main trends and advantages, and establishes the basic prerequisites for the active digitalization of risk management. The main factors of the positive and negative impact of digitalization of risk management, the main problems of the introduction of special software are identified. The author's classification of key digital solutions in the field of risk management is presented. The main ratings of programs in the field of risk management are considered. It is proposed to include the parameters "cost, architecture, integration, functions, users, opportunities for social interaction and security" in the risk management software rating system. The conducted research allowed us to confirm the hypothesis that the effectiveness of software implementation depends not only on the characteristics of the programs themselves, but also on the degree of readiness of the enterprise (in terms of the requirements of the internal and external environment) for their implementation. As a result, we received a methodology for assessing the feasibility of implementing risk management programs (IRM solutions), based on an assessment of the software itself, an assessment of the organization's readiness for implementation, and consideration of environmental factors. This approach allows us to comprehensively explore the possibilities of successful implementation of risk management software, accelerate and improve the efficiency of the decision-making process for choosing the necessary software, identify areas for improving the risk management system, as well as open up ways to sustainably increase the potential of the enterprise. The research contributes to the development of both the theory and practice of risk management, and to the development of a system for assessing the digital transformation of organizations.