Many firms are engaging in the digital transformation (DT) of their sales forces, and this trend has accelerated during the COVID-19 pandemic. However, research on DT as a profound organizational change process, as well as salespeople’s individual psychological reactions to such initiatives, is still limited. Although DT offers salespeople more and better resources for work-related goal attainment, it increases job demands and typically generates high uncertainty, which companies must then manage. We draw on job demands-resources (JD-R) theory to account for these bright and dark side effects simultaneously. We analyze the direct, mediated, and moderated effects of uncertainty reduction initiatives (resources) and excessive workload (demands) on the perceived usefulness of DT (i.e. salespeople’s motivation to embrace it), the stress it generates, and the ultimate success of DT integration. In doing so, we shed light on the complex pattern of relationships that characterizes salespeople’s psychological reactions to DT. Using DT context-specific constructs, we test our model and hypotheses on a sample of 144 salespeople of a firm engaged in DT. Our results fill several gaps in the technology in sales, DT, and JD-R literatures, and we provide managers with several guidelines to better manage DT in sales.