Theoretical basis The case is designed to be used with the digital business model framework developed by Peter Weill and Stephanie Woerner of Massachusetts Institute of Technology (MIT) (Weill and Woerner, 2015) and is referred to as the W & W framework. This approach provides a useful structure for thinking through the strategic options facing environments ripe for digital transformation. Research methodology Research for this case was conducted through face-to-face interviews with the protagonist, as well as through a review of their business planning documents and other data and documentation provided by the founder. Some of the market and industry data were obtained using secondary research and industry reports. Interviews were digitally recorded and transcribed to ensure accuracy. Case overview/synopsis The case follows the story of Kurt Waltenbaugh, a Minnesota entrepreneur who shared the dream of using data analytics to reduce costs within the US health-care system. In early 2014, Waltenbaugh and a physician colleague founded Carrot Health to bring together their personal experience and expertise in both consumer data analytics and health care. From the beginning, they focused on how to use data analytics to help identify high-risk/high-cost patients who had not yet sought medical treatment. They believed that they could use these insights to encourage early medical interventions and, as a result, lower the long-term cost of care. Carrot’s initial success found them in a consultative role, working on behalf of insurance companies. Through this work, they honed their capabilities by helping their clients combine existing claims data with external consumer behavioral data to identify new potential customers. These initial consulting contracts gave Carrot the opportunity to develop its analytic tools, business model and, importantly, to earn some much-needed cash flow during the start-up phase. However, they also learned that, while insurance companies were willing to purchase data insights for one-off market expansion projects, it was much more difficult to motivate them to use data proactively to eliminate costs on an ongoing basis. Waltenbaugh believed that Carrot’s greatest potential lay in their ability to develop predictive models of health outcomes, and this case explores Carrot’s journey through strategic decisions and company transformation. Complexity academic level This case is intended for either an undergraduate or graduate course on entrepreneurial strategy. It provides an effective introduction to the unique structure and constraints which apply to an innovative start-up within the health-care industry. The case also serves as a platform to explore the critical criteria to be considered when developing a digital transformation strategy and exposing students to the digital business model developed by Weill and Woerner (2015) at MIT (referred to in this instructor’s manual as the W&W framework). The case was written to be used in an advanced strategy Master of Business Administration (MBA) class, an undergraduate specialty health-care course or as part of a health-care concentration in a regular MBA, Master of Health Care Administration (MHA) or Master of Public Health (MPH). It may be taught toward the end of a course on business strategy when students are building on generic strategy frameworks and adapting their strategic thinking to the characteristics of specific industries or sectors. However, the case can also be taught as part of a course on health-care innovation in which case it also serves well as an introduction to the health-care payments and insurance system in the USA. Finally, the case can be used in a specialized course on digital transformation strategy in which case it serves as an introduction to the MIT W&W framework. The case is particularly well-suited to students who are familiar with traditional frameworks for business strategy and business models. The analysis builds on this knowledge and introduces students interested in learning about the opportunities and challenges of digital strategy. Equally, the case works well for students with clinical backgrounds, who are interested in how business strategy can influence changes within the health-care sphere. Finally, an important aspect of the case design was to develop students’ analytical confidence by encouraging them to “get their hands dirty” and to carry out some basic exploratory data analytics themselves. As such, the case requires students to combine and correlate data and to experience the potentially powerful combination of clinical and consumer data. Instructors should find that the insights from these activities give students unique insights into the potential for of data analytics to move health care from a reactive/treatment ethos to a proactive/intervention ethos. This experience can be particularly revealing for students with clinical backgrounds who may initially be resistant to the use of clinical data by commercial organizations.