Designing an innovation strategy in a world of rapid technological change has become increasingly challenging. Some companies are finding that anchoring technology choices in deeper understanding of the value users seek allows them to find a better balance among feasibility, viability, and desirability of potential solutions, and thus create more successful user outcomes. They do so by involving designers earlier in the roadmap development to guide product and technology selection, toward a future vision based on user value and aspirations. In this article, we extend two streams of prior research on technology roadmapping (TRM) and design roadmapping (DRM). First, we identify and compare technology and DRM approaches and their distinct strategic emphases: Technology selection and user value, respectively. Second, we compare two cases of DRM deployment in corporations: Siemens and Air France-KLM. The intent is to provide an in-depth understanding of why and how DRM complements TRM and how DRM facilitates making tradeoffs among strategic goals to more comprehensively address the feasibility, viability, and desirability of new product and service designs. We find that DRM embeds a deep understanding of current and future user needs, linking user-centered design and technology selection to strategy in practice.