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The paper describes the developed software product-the decision support system (DSS) «DSS Invect 2020» and its module «IT INVESTMENT», which can be used both independently and as part of the DSS «DSS Invect 2020». The DSS is designed to develop recommendations of the LPR during the selection of rational financial strategies by investors. «DSS Invect 2020» allows you to evaluate the attractiveness of investment projects in the field of digitalization of enterprises. The DSS «DSS Invect 2020» is made according to the modular principle. This makes it possible to supplement the DSS with other modules. The «DSS Invest 2020» program will allow forming a hierarchical view of the qualitative issue of choosing investment projects within the framework of choosing investor strategies using the DSS during the procedure for evaluating investment projects in the field of digitalization of enterprises, taking into account multifactorial factors.