The Fourth Industrial Revolution (4IR) has catalysed a paradigm shift in workforce demands, urging the cultivation of digital skills and human capital development. In South Africa, where a disproportionately young unemployed population coexists with a reported gap in skilled labour supply, the urgency for mass upskilling and reskilling is paramount. The private sector (i.e. industry) has a critical role to play in this regard. Yet, limited data is available to illustrate the involvement of South African businesses within the education ecosystem, the extent of their activities related to human capital development (including digital skills development), or the effectiveness of their related activities in this regard. Focusing specifically on medium-sized organisations, which are envisaged to contribute greatly towards job creation in the country, this study explored the approaches of these organisations (consisting of 51-250 employees) toward human capital development and the integration of digital skills in the face of evolving work landscapes. Using interviews with key informants and a structured survey of 61 organisations across diverse sectors, the findings revealed that while most organisations offered some form of digital skills training, a notable portion lacked comprehensive structures for organisational learning. Challenges to effective implementation include resource limitations, awareness gaps and resistance to change. The study underscores the crucial role of youth employment accelerators in bridging the gap between inexperienced youth and resource-constrained companies. Additionally, it highlights the need for cultivating soft skills alongside digital competencies. These insights shed light on the nuanced landscape of digital skills development among medium-sized South African organisations, emphasising the imperative need for tailored policies and initiatives to support their pivotal role in driving economic growth and innovation in the 4IR context.