The growth of the cloud technology market is driving a change in the strategies of IT companies. Previously, the priority for companies was on-Premises corporate information systems, i.e. systems delivered according to the SaaS model (Software as a Service). In positioning the benefits from the solution, the primary thing becomes dialogue with customers regarding economic benefits, rather than the functionality of the system. The implementation of new strategies forms the training requirements for employees. The article aims to develop a training program for IT employees of an international supplier of corporate systems. The analysis of scientific sources on the research topic is carried out, the problems are described, and the lack of scientific knowledge is highlighted in the use of Design Thinking methods for IT training. The use of system analysis made it possible to formalize the research tasks. The set theory was used to formalize the problem model—sets of subject areas and their characteristics are highlighted. To achieve the research goal, the methods of Design Thinking were applied. The article describes the study structure in terms of surveys and interaction with respondents using the methods of Design Thinking and the subsequent analysis of the data. The proposed methods, based on the assessment of the company's management, made it possible to increase the effectiveness of the survey in terms of employee engagement. During the Design Thinking seminars, hundreds of subject topics were formalized, and dozens of topics were selected that corresponded to the set goal. The selected topics formed the basis of a training program for the IT staff of an international provider of corporate systems. Based on the feedback gathered from the staff, the seminar was highly appreciated. Positive reviews and results confirm that the goal of the study was achieved, and the methods used are more effective than those used previously.