As technology continues to advance and improve, marketing trends are beginning to shift into the digital space. Addressing the generation gap within digital marketing, this paper reveals the latest digital strategies being utilized, while comparing results from marketers and the younger generation targets they are trying to hit. Both groups were asked a series of nine questions ranging from the following topics: basic demographics, difficulties faced in digital marketing, views of the industry as a whole, as well as opinions on the digital age gap. Data was collected separately and analyzed quantitatively to provide further insight. Solution paths and methods for further research are concluded: Incorporating both traditional and digital in all marketing strategies Hiring recent college graduates in marketing firms to help connect with the younger generation Keeping the older generation informed with the latest technologie