This report explores how Reader’s Digest Canada’s digital strategies are used within an existing brand framework to adapt to a diverse and changing media landscape. Using a case study of a direct marketing effort, the RD Sweepstakes (Sweeps), the effects of digitization on the development of new business opportunities are explored. With direct marketing practices following a digital trajectory (in response to audience migration to online platforms), the Sweeps has gradually carved out a niche of its own. This report reaffirms the marketing function of the Sweeps as well as argues that the Sweeps is a vertical capable of generating its own direct revenue. By citing market research and beta testing in the United States and Canada, two monetization models for a stand-alone Sweeps product are considered. Conclusions are drawn that demonstrate the viability of a Sweeps mobile application while taking heed of legal implications, market context, and overall brand equity