This case narrates of the innovative journey undertaken by Chemical Industries Education and Training Authority (CHIETA) and the Johannesburg Business School (JBS) to facilitate the transformation of small and medium enterprises (SMEs) in South Africa in the context of Society 5.0. The key task in this journey was to promote the integration of advanced technologies in SMEs operations to enhance societal and economic growth and sustainability. The project was initiated in 2023 by CHIETA and led by Professor Arnesh Telukdarie and his team at the JBS to address the digital skills gap among SMEs across South Africa. CHIETA provided Professor Arnesh’s team with a database of 400 chemical SMEs in a project that aimed to help improve the SMEs digital capabilities and contribute to the growth and sustainability of not only the SMEs but also communities at large through digital innovations. The project began with a comprehensive data collection from the 400 SMEs. A questionnaire was sent to the SMEs with regard to their existing digital operation, as well as the digital tools they wished to implement into their systems. The responses given by the SMEs were used to tailor a two-phased training for the SMEs which was aimed at improving their understanding and integration of digital transformation and Society 5.0 concepts. This case study is a learning tool that is designed to narrate how this project was handled together with the current progress of CHIETA and JBS in implementing Society 5.0 training.