This document contains the data set for the author's article, "SME's and Supply Chain Digital Transformation: Challenges and Opportunities." The data set includes the questions and responses to a survey implemented with companies in the Evansville surrounding area. The study examined the particular challenges facing SMEs in a specific geographic region as they begin to move toward digital transformation, with the goal of gaining insights that are useful for other SMEs and contribute to the body of knowledge about this topic. The study was guided by an update to the three-dimensional People, Processes, and Technology Framework for organizational change that includes strategy formulation. Results of the study point to the role of third-party financial and consulting support for SMEs seeking to undergo supply chain digital transformation; as well as the crucial role of digital transformation strategy formulation that specifies the roles of and impacts on people, processes, and technology. Strong support for employee skill upgrades in particular also stands out as a major outcome of this study, pointing to training as a “jump starter” for SME companies seeking to move forward with digital transformation, and implying the importance of a proactive role for outside entities like local universities, government agencies, or consultants who can provide training support.