Digital Transformation (DX) has become a pervasive global phenomenon that is having a profound effect at all levels of an enterprise. The umbrella term DX is supported by nascent technologies such as blockchain, Internet of Things (IoT), and cloud-based computing and networking. The speed by which these new DX technologies have emerged has challenged current technical infrastructures, budgets, and skillsets as organizations attempt to incorporate and implement these technologies as part of pervasive digital operational initiatives. DX also includes the transformative effects (deployment and adoption) of these technologies, and these are referred to as "outcomes" in this dissertation. Not surprisingly, recent studies indicate that at least seventy percent of DX projects either fail or underperform. As firms assess existing technology-to-business alignments in search of attributable causation, they discover that these alignments are often opaque regarding the capabilities required to obtain optimal digital transformation outcomes from the application of specific technologies. This is especially true as underlying technology infrastructures and architectures, which have had a traditionally functional role such as the data network, are increasingly relied upon to support the strategic outcome requirements of DX. This dissertation uses an inductive, multiple case study approach to explore these relationships and outcomes. It directly observes a set of large organizations across multiple verticals. These organizations have all completed pervasive digital transformation initiatives, more specifically, this study measured the resultant levels of vi