Motivation to change plays a significant role in digital supply chain transformation (DSCT) endeavors. In this chapter, we analyze a multidimensional framework formed along four dimensions (namely, discomfort, survival anxiety, learning anxiety, and psychological safety) in two stages (namely, momentum and continuity). As a research methodology in this study, we use a multiple case study of 17 international large case companies. We collected data from semi-structured interviews and secondary data. Psychological safety is the most important dimension of a successful DSCT. Our findings also reveal that, in the momentum stage, successful companies involve operational employees in developing a DSCT vision, providing formal training to support digital expertise, and adjusting their information technology (IT) infrastructure to connect end-to-end digital initiatives. In the continuity stage, successful companies establish a balance of realizing value-add and enabling continuous change by supporting an entrepreneurial environment, continuously updating IT infrastructure, and providing stable role models for the operational employees. This chapter provides significant actionable insights on how to successfully enable motivation and effective DSCT.