Digital technologies and techniques have matured to the point where they support major organizational redesign, and early adopters have captured competitive advantage by using them. Thus, organizations now recognize they need to drive large digital transformation events. Two kinds of digital transformation are taking place in businesses today. One aims to change the way a company competes. The other kind of transformation aims to modernize a company’s technology and supporting functions so that the company can transform to a digital environment. Both kinds of transformation are journeys to new operating models, and those journeys take time and rethinking of all aspects of existing models. Most organizations find the enormity of change becomes is overwhelming. Let’s look at how the successful companies are managing their IT modernization.