Smart service systems have been dealing with various wicked social and cultural problems by providing diverse solutions for society. Cargo transportation is one of the most challenging issues in logistics; in this paper, we explore multiple stakeholders’ information environments surrounding containerized cargo transportation by a design thinking approach. Throughout the analysis, the latent problems are summarized in the following two manners: (1) miscommunication with inefficient information flow among multiple stakeholders; and (2) a lack of resource management coordination among service providers. With these two identified problems, the objective of this work is to develop a prototype information and communication technology-based service application for both trucking companies and customers. This work makes two contributions. First, it methodologically proposes a customer-centered design approach for logistics management by adopting a design thinking approach. Second, it suggests a practical ICT-based solution for the mentioned problems.