Book excerpt: Businesses are increasingly embracing the dynamics of digital technologies, as they communicate with interested parties about their responsible initiatives through corporate websites, social media platforms and other interactive channels. Therefore, a quantitative study involving 202 owner-managers investigates their attitudes toward stakeholder engagement through digital media. The research methodology involved the integration of previously tried and tested measurement tools from the technological acceptance model, the pace of technological innovation and corporate social responsibility (CSR) items, to better understand the rationale for using digital media to communicate with stakeholders on the organization's responsible behaviors. The results have indicated that there was a positive and significant relationship between the perceived “ease of use” and “usefulness” of online media. The findings also revealed that the younger owner-managers were increasingly using ubiquitous technologies as opposed to their older counterparts. This contribution implies that all businesses, particularly the smaller ones, could improve their relationships with stakeholders if they use digital media to communicate about their responsible behaviors.