This article uses mini- case studies of three early stage organizations that pursued different pathways or models for bringing emerging, transformative digital technologies to the healthcare market. These organizations were each focused on different applications of digital health: Stentor was a venture capital backed, university spinoff focused in the field of digital radiology; Omnyx was formed as a joint venture (JV) by an academic medical center and industrial partner to transform the field of digital pathology; and, IBM Watson operating as an IBM unit, focused on the promise of artificial intelligence and machine learning for broad uses in cancer diagnosis and treatment. Each took a different organizational and business model path that resulted in mixed outcomes. While there are always many reasons for success or failure, we observe that these digital healthcare markets are more complex than typical consumer or technology markets. While any solution in healthcare demands patient centricity; healthcare markets additionally require a strong understanding and appreciation of the supporting ecosystem or network consisting of physicians and providers; and of constraints from payers and regulators. The value propositions of each member of the ecosystem must be understood and addressed. To meet this challenge, we advocate the formation of an integrated multidisciplinary commercialization team that addresses the multidimensional value proposition across the company life cycle. And importantly, that team should work collaboratively, and include service design as a key team member - along with the technology, business, marketing, reimbursement, and regulatory components.