Industry 4.0 has been evolving and affecting various sector globally, one of them is logistics sector. On the other hand, Indonesia needs to solve its logistics problem regarding the amount of costs that needs to be allocated to logistics activities, mainly transportation activities. A solution for the problem is by using the development of ICT, and Internet of Things (IoT) is one of the options. The main purpose of this study is to find a design of implementation strategy for IoT on logistic transportation sector in Indonesia, based on its Key Success Factors (KSF). The study is divided into two, identification and prioritizing KSF using Analytic Network Process, and designing the strategy. In the first stage, the result indicates that there are eight main KSFs which affecting the implementation of IoT in logistics transportation sector the most. In the second stage, the eight main KSFs could be used to generate various strategies which then be designed into a structural strategy implementation diagram using Interpretive Structural Modeling. The results of this study are the finding of eight main KSFs which are change in business mindset; employees‟ commitment; performance‟s quality; training; competition; involvement of top management; on-time delivery; and clear standard on architecture reference for the IoT system, and also the discovery of implementation strategy diagram that consists of eight main strategies which are change management; training; HR management; building cooperative relationship with partners; maintaining and improving the company‟s system; establish a monitoring system; forming a fail-proof system; and designing a standardized integration system.