The disparity between digital transformation leaders and laggards stems from a complex web of overlapping factors -- which often speak more to organizational issues than technical difficulties. Considerations in play include corporate history, IT philosophy, the ability to deliver on customer experience and a product vs. project mindset. A particularly important element separating a successful digital business from its competitors is a knack for translating small successes into enterprise-wide benefits. Indeed, overcoming digital transformation challenges at scale is crucial for realizing the promise of technology-infused business models, according to CIOs and industry analysts. Companies playing catch-up in the digital race must first focus on the essentials, such as customer experience, before moving on to more innovative pursuits.