In the past, technological tools were considered a "solution" to advising challenges. However, successful advising transformation efforts have also incorporated shifts in institutional culture and workforce in addition to the adoption of new technologies. Approaching advising redesign as a digital transformation (Dx) initiative can transform an institution's operations, strategic directions, and value propositions surrounding advising. This chapter articulates an approach to the implementation of advising technologies and the necessity to view "holistic advising redesign" as a Dx initiative for advising to reach its full potential at scale. For institutions, this means embracing not just the promise of new technology but also the investment in and attention to the critical shifts in culture and workforce.