The evolving retail landscape in the digital age has resulted in opportunities and novel capabilities for retailers. This paper identifies four key challenges facing retailers based on insights from practitioners and academics using the customer journey framework as a guide. It then considers evidence from both practice and theory on how contemporary retailers might best innovate in the face of these challenges, to get “the right message to the right shopper at the right time.” Historically, retail was largely constrained to focus on individual touchpoints as manufacturers drove the majority of communication decisions. More recently, with the ability of e-commerce to capture the shopper decision journey more comprehensively, retailers are better able to understand what the right message would be as well as where, when, and how to deliver it to reach the most responsive shoppers to achieve the retailer's strategic objectives in each phase of the journey. It is within this context that this paper considers the following key challenges: 1) When is the right time to communicate with a given shopper?, 2) What is the right way to communicate with a given shopper?, 3) What is the right way to leverage in-store collateral?, and 4) How do we cultivate the right long-term relationship with a shopper?