In this paper, we synthesize an effective communication prototype that deals with some challenges in the container-trucking sector in Egypt, mainly multiple stakeholders’ communication problems associated with waiting time. Container-trucking is one of the most important activities in logistics management. However, Information and Communication Technology (ICT)-based methods are very limited to identify the latent communication issues in this sector in Egypt. To address these issues, we conducted a design thinking methodology in order to understand multiple stakeholders’ requirements, using qualitative research techniques. As the results, we found that the main problems faced by customers are trucking company selection, miscommunication, and the lack in the information flow, while the main problem faced by trucking companies is the fluctuations in resource utilization. Based on this, we developed a web-based prototype to represent the core features and functions to improve communication in both Business-to-Business (B2B) and Business-to-Customer (B2C). Consequently, this paper has two main contributions. First, it applies design thinking approach to a logistics problem and presents an IT-based solution for it that will reduce processing time. Second it increases customer satisfaction and improves resource utilization in the trucking companies.