The digitalization of the shipping industry represents a significant technological transformation that is comparable in impact to previous technological shifts such as the move from sail to steam and from steam to motorization. In addition to the direct alteration of fundamental shipping processes, digitalization also affects customer relationships, internal operations, and value propositions. This study focuses on the transformative potential of digital technology in the shipping industry, particularly in terms of its impact on shipping strategy and business models. To fully understand the digital transformation in the maritime industry, we suggest in the conclusion an analytical model based on the fundamental assumption that the driver in digitalization concerns Shifts in Costs (SiCs). The analytical model includes insights from maritime business models, shipping technologies, and digital innovation. The concept of SiCs served as a starting point in order to examine the critical economic consequences from the transition from analog to digital representation that is the driving force behind the shift toward digitalization. Along with the development of novel, redefined business models and streamlined organizational processes that generate or capture extra value for the shipping companies and stakeholders, the ability to capture value and invest in new digital services and products also depends heavily on decision-makers’ mindset and external knowledge of the innovation itself. Expanding one’s mindset is essential for the innovation journey to generate improvements from data-driven innovation by accessing new digital platforms and learning about innovations that might otherwise remain unknown.