The aim of the research is to theoretically substantiate the need for an in-depth assessment of the current organizational potential of a company in order to successfully conduct digital transformation. The study is based on a method developed by the authors for assessing the current organizational potential in accordance with the requirements and characteristics of the digitalization process. The method includes an extended classification of management problems in conditions of increasing uncertainty and the rate of change in the business environment, a methodology for assessing (calculating quantitative values) the main parameters of the Digital Transformation Snake model (DTS model), a graphical representation of a digital transformation model based on improving the organization’s personnel structure. The DTS model includes the identification of two zones of organizational impact on the workforce of the organization: the zone of restructuring of the workforce and the zone of personnel development. The conclusion is made about the use of various technologies for improving the organization’s personnel to achieve a successful digital transformation. Technologies are distributed across the designated areas of organizational impact.