Structural changes are a key element of digital transformation and affect value creation paths such as digital agility. Scaling agility constitutes such a structural change. Research has highlighted the need to increase our understanding of the underlying changes to understand the microfoundations that undergird digital transformation. Thus, we look at how scaling agility affects value creation paths by answering the question, “How does the structural change of scaling agility affect changes in value creation paths in digital transformation?” We conduct a multiple case study with four organizations. The study surfaces three observations of this structural change that enable digital agility: Cross-functionality to allow for the emergence of creative ideas, fostering self-organizing to seize digital opportunities, and higher value chain interconnectedness for improved delivery. Furthermore, we identify two barriers as inhibitors of such transformations: complexity trap and resource foundation. We contribute to understanding digital transformation and provide valuable insights for practitioners.