This chapter explores the role of owning families in the digital business transformation of family firms, illustrating how they influence its implementation and success. Digital business transformations represent a key challenge for businesses today and special attention needs to be paid to the context of family firms. The literature shows how the age of digital technologies not only shapes business environments, but changes entire business models. The authors focus on the digital readiness of the organization’s culture as a vehicle for successful digital business transformations by arguing for the significant role of the owning family’s openness towards new technologies. Further, they argue that the digital readiness of the organizational culture also depends on the business sensing capabilities and willingness to change instilled by the family’s openness to novelties in the digital arena. Implications and future research directions are discussed.