The role of a college president is unique and challenging given the demands of the position as well as the shifting higher education landscape. Research shows presidents are expected to fill many roles in a college community including fundraiser, financial steward, problem solver and cheerleader (Selingo et al., 2017; Trombley, 2007). As the United States becomes more reliant on digital communication, presidents are expected to conduct much of their essential engagement on platforms such as videos, websites, blogs and social media (Ahlquist, 2017). The purpose of this multiple-case study was to examine the unique role a president's digital engagement plays in fostering a sense of community among stakeholders. This multiple-case study included interviews with presidents who exemplified best practices at institutions nationwide as well as members of their senior leadership teams. A document analysis of digital communications helped to corroborate and add texture to the findings. Understanding the importance of presidential digital engagement has the potential to influence best practices at colleges and universities nationwide at a time when many institutions need to distinguish their unique offerings and cultures in light of a declining number of high school students in the United States (Will, 2016).