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Arist was a Boston, Massachusetts-based startup with a text message learning platform. It was founded by three undergraduate students and raised more than $3.9 million in funding during its first three years. The inspiration for Arist was the lack of learning opportunities for young people in war-torn Yemen where schools were closed and access to high-speed internet was limited. After much research, testing, reflecting, and pivoting, the Arist team made an exciting discovery: Not only would a short-form SMS approach to teaching likely be desirable in regions such as Yemen, but this approach could also be valuable to well-funded Fortune 500 training and development organizations. According to research referenced in the case, more than 12 years after the introduction of the iPhone, not only had SMS sustained popularity, but businesses were increasing their SMS spending for marketing and other uses. Early clients included Dupont and the State of California. The founders recognized that a focus on the needs of large, for-profit companies in the United States would not directly address the learning needs in education-challenged regions such as Yemen. However, they hoped that by building a text-message-based learning business in the United States, they would one day be able to recruit professors to create courses for interested students worldwide, delivered through the Arist platform.

Commonwealth Shakespeare Company (CSC) is a performing arts non-profit organization founded in 1996. It has a strong and presumably loyal following for its annual outdoor production of Shakespeare, called Free Shakespeare on the Common. However, it has limited data to prove this and to cross-promote its other for-fee services. The data it has is held in various databases. Further its analytics and marketing resources are limited. Meanwhile, pressure on the live performing arts industry continues to mount as digital entertainment options grow. Recognizing the disruption that is underway, CSC begins to explore virtual reality's potential and influence on the performing arts. In 2017, while consulting for a team at Google, CSC's founder and a team at Google determined it would be valuable for all parties to produce and release a virtual reality version of Hamlet. With the support of Google and a few major donors, the Hamlet 360: Thy Father's Spirit project was released in January 2019. The case centers on CSC's struggle to meet immediate responsibilities while exploring new digital models and their potential value to and influence on the performing arts. The case is designed for classroom discussion but is also well-suited to student projects related to digital transformation, mobile app design, and more.

MDSC is a 501(c)(3) organization, professionally staffed with a mission to ensure individuals with Down syndrome are valued, included, and given opportunities to pursue fulfilling lives. Though dedicated to the families of Massachusetts, MDSC is gaining recognition as an innovator and being called upon to train and support organizations in other parts of the US and world. When the case opens, MDSC's executive director, Maureen Gallagher, is departing a strategic planning retreat. She and her Board members have come up with an exciting list of strategic initiatives, including areas for potential service expansion. However, current initiatives and needs of its steadily expanding community were beginning to overwhelm the current operational model. MDSC had the know-how, the ideas, and the drive to do more, but this operational reality would constrain further service expansion. In addition to specifying three overarching directives and four specific strategic initiatives to support these directives, the board also determined that MDSC would move to a state-of-the-art approach to support its growing list of state-of-the-art services. The approach would include a revamped operational model built upon an updated digital platform. With these changes, MDSC would be able to scale its services to families, increase its donations, and win more grants to help sustain the organization's good work. Though there is consensus in the vision, there are questions regarding the steps this small, resource-constrained organization should take to make this vision.

GasBuddy is a 15-year-old mobile app-led company, providing gas station and pricing information to drivers and selling ads to fuel stations and convenience store owners. Though the GasBuddy Mobile App has received many awards and often ranks among the top-three travel apps in downloads, competitive pressure is building. Recognizing the competitive shifts, its parent company, UCG, brings in a new management team that is steeped in start-up experience spanning payments, convenience stores, social and mobile media, digital transformation, point of sale systems, modern technology platforms, agile development, and UI/UX. The new team recognizes that speed as well as agility will be essential for future growth. The case takes readers through the company's cultural, digital platform, and product line changes, including a bold entry into the payments industry. The changes support the company's evolved branding and a new multi-sided platform (MSP) business strategy. Early changes across the three areas - culture, digital platform, and product line - are put to the test during highly destructive Hurricanes Harvey and Irma.