In Part II of the Roundtable on Digital Advertising, the academic and industry participants detailed the breadth of skills students need for advertising. The conversation moved to authenticity, in light of how celebrities and social media influencers have taken a central role in advertising today, especially among Millennial audiences. The roundtable then focused on how technologies have caused the advertising industry to adjust its strategies many times throughout history. To conclude, participants agreed that digital technologies and media have wrought rapid changes in the last 20 years. However, one should take caution in making definitive claims on what will come for advertising's futures because the industry and the academy are still sorting out how Big Data, algorithms, and automation will impact business and everyday life.