Due to the combination of vast technology trends brought by Industry 4.0, present-day consumers need and stiff global competition and require businesses from across many industries to constantly innovate. Clients request multifaceted support from manufacturers and service providers while the transition towards new symbiotic ecosystems disrupts traditionally established processes in some sectors. This is largely happening in the global automotive industry where in-car and around-the-car services with asset-sharing concepts are taking a dominant role rather than plain vehicles sales and car ownership. In our paper, we investigate the possibilities of new and improved business collaborations between a car retailer operating in several European countries and its SME (small and medium-sized enterprises) customers across various sectors currently owning car fleets of at least five vehicles. We test several hypotheses and conduct a systematic statistical analysis of the proposed business model’s aspects on the sample of almost 200 SMEs from five countries in Southeast Europe. By using the χ² test and a one-tailed t-test we tested both frequency data and the continuous variables. Research indicates that SMEs look for new ways to organize their fleet management strategy more efficiently and thus more precisely plan associated costs. Regardless of the country of origin, SMEs want to explore a business model with more introduced to their fleet management and are ready to accept new technologies for fleet management operations.