The path to becoming a digital company is difficult and the challenges are multifold. It means ensuring customers remain connected even with the drastic changes that may be needed and overcoming resistance to new business models. Becoming digital does not simply mean implementing new technology; it also requires developing new leadership skills combined with connectivity among a company’s people, proc­esses, and data. Cultural changes may also be a challenge if the digital transformation must cut across silos in the organization. This Advisor’s case study examines the implementation of a digital change in a US community bank meant to retain its loyal customer base and to put in place newer ways of monetization.