As #5 on Fast Company’s Most Innovative Companies in Healthcare, Dexcom provides life-saving digital tools to help people manage their diabetes. Despite its positive impact in the lives of early adopters, Dexcom’s core technology, continuous glucose monitoring or CGM, had yet to reach the mainstream of diabetes care. Dexcom engaged Upstream to help move their products and services from early adopters to the mainstream. To support this goal, Upstream engaged executives and a cross-functional team in stakeholder interviews and a customer journey mapping workshop to frame the barriers to product adoption and continued use. We then validated and refined the journey framework through in-depth journey interviews with patients and physicians. Some of the barriers included a lack of product awareness, a disconnect between data CGM provides and the daily decisions and behaviors of diabetics, and a belief among primary care physicians and diabetics that CGM is only useful for preventing extreme cases of hypoglycemia. The journey framework that emerged was used to identify key opportunities across the continuum of experience and prioritize cross-silo opportunities to open the mainstream market.