Enterprise sustainability is a key aim in the fourth industrial revolution era, requiring a new approach based on intelligent technologies that considers the new roles of leadership and sustainability as well as the new trends in emerging smart technologies, with a new focus on Society 5.0. Smart parking has a significant role in fostering the determinants of sustainability in public parking enterprises and achieving adequate mobility in smart cities. Thus, smart parking is the subject of the research presented in this paper. This study defines the vital processes, including leadership processes and technologies needed for smart parking, managed by innovative public parking enterprises. Having this in mind, trends, key facts, the results of present innovative technology enterprises, and methodologies for designing and establishing smart public parking enterprises are analyzed. This paper aims to determine the sustainability of parking enterprises in their current states by developing a MORSO methodology. The MORSO methodology includes independent variables, including the leadership level of the intelligent technologies used, quality of the business processes, and risk related to the business processes, and a dependent variable, the sustainability of smart public parking enterprises. The MORSO methodology also includes steps for the definition of indices related to variables that could be assessed by appropriate techniques such as using questionnaires. Finally, the MORSO methodology introduces steps by which statistical approaches and artificial neural networks (ANN) are applied to test hypotheses regarding correlations between independent and dependent variables. The results of the presented model case study application show that there are strong correlations between smart sustainability and leadership (0.769), quality (0.904), and risk (−0.884), respectively. Additionally, at the level of the presented case study, the results of the application of the ANN indicate that the values of the dependent variable in the following time period can be determined with high accuracy, based on the knowledge of the values from the previous period, with a regression coefficient value of R = 0.99482. Finally, in this way, the transition from existing public enterprises to sustainable smart public parking enterprises is envisioned.