Consumers’ attention is more divided than ever, and the value of that attention has reached unprecedented levels. The Internet has changed the way we communicate, the way we amuse, and the way we live. And, as a consequence, both the entertainment industry and the advertising industry are being forced to redefine their relationship and their bonds with audiences. This has put severe pressure on how they operate as they try to adapt to a new scenario mainly characterized by unpredictability. Using data from 13 semi-structured in-depth interviews, this paper explores the transformation of the advertising industry in the “digital age” by means of examining practitioners’ narratives related to business models, relationship with consumers, metrics and analytics, organizational structure, and the integration of digital and traditional strategies.