The digitally savvy company will adopt competencies from ‘born-digital’ successes like Amazon; ‘disruptive’ successes like Apple and ‘cross-over’ successes like GE. It will challenge prior investment strategies and be ready to shutdown traditional business streams in order to create new digital products and business models. Becoming digitally savvy requires a pilot. Even with a company of millennial digitally-aware staff, technology needs an advocate. The challenge is not normally the new hires, but making the C-suite and executive teams digitally aware. A company needs someone who has the executive profile to take the company from current state to digitally savvy state. The CIO can and should be the catalyst that increases the rate of travel towards the digital savvy destination.