Perishable product last-mile transportation is less-thantruckload as relatively small goods are shipped in small batches that can be bundled with each other to increase the filling rate of the trucks’ capacity. However, the large number and frequency of trips entails low profitability and environmental sustainability of the companies operating perishable product supply chains. This is mainly due to the fact that the trucks are partially loaded or empty during their trips. The present paper provides a preliminary analysis of the main issues in the perishable product supply chains and propose collaboration and asset sharing as key approaches that can provide operational and economic benefits to all the stakeholders (shippers, carriers, customers) of a regional distribution network. A prototype of new technological multi-sided system has been designed. It consists of two subsystems: (i) carriers can use a multi-product daily assignment and routing system that provide input data to a simulation-based distribution scenario analysis tool for complex transportation scenario analysis and optimization; (ii) customers and producers are provided with an online asset sharing tool (experienced by web platform and mobile application) based on a transportation estimate management tool and a real-time marketplace. Potential advantages of collaboration and asset sharing by using the proposed system in perishable product supply chains are investigated.