Since the late 20th century, the introduction of digital technologies has revolutionized the way people interact with the world. This has led to the mass diffusion of the Internet, smartphones, global computer networks and virtual reality, which have become an integral part of people’s daily lives. This digital transformation has had a significant impact on all spheres of human activity, including work. In addition, unexpected events such as the COVID-19 pandemic forced organizations to digitize rapidly to conduct business, despite social restrictions. This has contributed to the emergence of new paradigms in the world of work. In manufacturing sectors, the industry 4.0 model using automation, robotics, artificial intelligence, the Internet of Things and additive manufacturing has enabled manufacturing companies to optimize processes, reduce costs and improve service efficiency. While digital tools have a positive impact on economic and environmental aspects, they also force organizations to reconceive the role of human activity in the workplace. This revolution in the world of work can, however, have both positive and negative implications for an organization’s human resources. It is the responsibility of organizations to choose whether to adopt a sustainable approach that balances economic, environmental, and social factors. Specifically, to preserve social sustainability, organizations should adopt human resource management practices that place human capital at the centre of the transition to digital workplaces. This requires providing employees with digital skills for decent and rewarding employment. This paper aims to provide an analysis on the topic of digitization and social responsibility, where humans are at the centre of interest for organizations. Conflicting views on the effects of digital transformation on social sustainability make this an important topic for research. To investigate this gap, we adopted a two-stage methodology. In the first stage, we conducted a systematic literature review to understand the most widely discussed research topics on the topic to date. Then, based on these findings, we conducted an exploratory case study. Specifically, this paper analyses a San Marino company operating in the medical sector. This case is particularly interesting in that it highlights the effects of social sustainability related to digital transformation, both from the perspective of the organization and the beneficiaries of the product/service. The case study will allow for feedback and empirical validation of what is known in the scientific literature.