Digital Health companies have captured the interest of many stakeholders in the medical and technology communities, not least of which is investors. Other stakeholders include government regulators, clinicians, health care administrators, patients, and payors, all of whom have differing expectations of the digital health sector. The unconstrained term “digital health” covers a “Wild West” landscape of non-traditional solutions and services and encompasses multiple areas ranging from clinical workflow enhancement systems to digital therapeutics. With only a handful of long-term success stories in this nascent industry, the following discussion examines some considerations for the effective commercialization of a digital health product and presents a case study on a successful pioneering company, iRhythm® Technologies Inc. The reader will 1) understand how the complexity of traditional medical technology sales extends into digital health, 2) learn from a practical case study and 3) be exposed to emerging commercialization models in this new space.