On January 11, 2017, Waseda University launched a university–industry collaboration program with a local government body in Kitakyushu City, Japan and 20 local businesses in the area. Officially called the “Waseda University IPS Kitakyushu Consortium (IPSKC),” the program aims to change the direction of local society and to develop innovative business and technology solutions in the era of Industry 4.0. In addition, it seeks to contribute to future global business development with neighboring Asian countries. As a first step, one of the program’s key initiatives was to offer consortium members an Internet of Things (IoT) business modeling workshop as part of the University’s industrial IoT/business engineering education program. This paper discusses an approach to facilitate workstream as a case study. We present the key results of the workshop; and discuss the future outlook of IoT and PLM education program.