Decision support systems and automation of management processes are very much in demand in the last decade; however, this demand is not covered with professional services yet. Society becomes more and more data-driven and the application of automated development processes and project monitoring processes underlines a need to apply changes in decision-making and apply different models and tools to this domain and expand it for various business processes. The study of the improving software possibilities for project management and analysis of software and existing technical capabilities was carried out in this work. The review and outlined models allowed us to identify the main directions of software development and outline the theoretical basis for the implementation of the plugin for Jira administration. The development of the software add-on based on the fuzzy logic models represents the novelty of the research. Applying the proposed DSS system will reduce the time required to analyze the situation before decision-making. The introduction of similar systems into software development makes the business more dynamic and gives an advantage over competitors.