Customer engagement (CE) is an increasingly studied topic in marketing that relates to the attitudes, behaviors, and connectedness of customers to a firm and to the firm’s other customers (i.e., the marketplace; see Kumar et al. 2010; Kumar and Pansari 2016; Van Doorn et al. 2010). CE has become an important topic because it reflects the increased ease with which business-to-consumer (B2C) customers (largely empowered by new technology) can engage with firms and other customers outside of face-to-face interactions. Overall, this is seen as a positive change—firms want better access to, and deeper relationships with, customers, and technology-driven CE facilitates this (Kumar and Pansari 2016). However, this development brings with it uncertainty regarding the future of B2C salespeople and the organizations that employ them because, traditionally, the sales force has been a firm’s primary method of engaging customers. Research by Beatty and Smith (1987), for example, showed that in the past the bulk of a customer’s external information search came from in-person sales interactions. However, more recent work suggests that this is no longer the case, as customers now enter sales interactions much later (57–۷۰% of the way through decision) and after considerable prior engagement (Microsoft 2015). With customers now entering sales interactions highly engaged and informed, the question is, where does this leave the B2C salesperson? While research is limited on this issue, industry reports have predicted that firms’ newfound focus on CE outside of sales interactions is contributing to the demise of direct selling. For example, a report by Forrester Research suggests that one million, mostly order taker, sales jobs will be lost by 2020 (Hoar 2015). This decline is predicted because customers can now self-educate and make decisions separate from the sales interaction, which is precipitating a move of their purchasing activities to e-commerce sources. This point is further emphasized by a McKinsey report that reveals that car shoppers today visit only 1.6 dealerships before making a purchase decision (compared to 5 dealerships just a few years ago; Economist 2015). Figure 9.1 visually represents changes to how customers engage, within and external to sales interactions. The issue addressed by this chapter, how CE outside the direct sales interaction impacts CE inside the interaction, is important for reasons far beyond academic interest. If these doomsday prophets are correct, success in encouraging CE external to the sales interaction is ushering in the end of direct selling. While this may be a goal for some firms, we contend that diminishing direct CE also portends a decrease in the quality consumer decisions (i.e., decreased value) that has traditionally been a benefit of in-person sales interactions. In order to explore this important and timely issue, we held a focus group with executives in the retail jewelry industry on the topic of the challenges involved in selling to engaged customers. The themes developed from this focus group run counter to suggestions in the literature that salespeople who act as “knowledge brokers” will be successful in creating value with their customers. In fact, the findings indicate that for customers highly engaged outside the sales interaction, a salesperson’s efforts to engage within the face-to-face interaction may actually impede, rather than create, value. Thus, in the remainder of this chapter, we start by reporting the key themes that emerged from our focus group study. Concurrently, we introduce literature related to each theme and then propose a conceptual, literature-based solution to these key challenges by drawing upon research on CE, personal selling, and psychology. A summary of the main literature referenced is detailed in Table 9.1.