Successful commercialization of medical technologies increasingly requires developers and manufacturers to think early-on about regulatory approval and reimbursement strategies for their new devices. This can be particularly challenging in the case of monitoring devices, where demonstrating the effectiveness and finding the coding and coverage can often be a complicated and lengthy process, particularly with the given current reimbursement policy. In this paper, we use three technology case studies to examine how firms are navigating the status quo and illustrate the importance of incorporating a comprehensive understanding of current market and regulatory constraints into the development and commercialization process. The case studies suggest that viable approaches can include pairing a monitoring technology with a therapy, or relying on hospital-pay or patient-pay models that are based on demonstration of direct benefits or cost-savings to these parties. The results emphasize that successful innovation in monitoring technologies increasingly requires a very closely aligned engineering, business, and health-economic strategy. Developing a comprehensive understanding of the specific value drivers and policy-induced constraints can contribute substantially to achieving the true benefits of monitoring technologies.