Digital transformation is critical for businesses, enabling the integration of technological solutions to improve processes, customer experience, business models and overall organisation. Enterprise Resource Planning (ERP) systems such as SAP Business One (SAP B1) are at the heart of digital transformation. These systems integrate various business functions such as accounting, financial management, procurement and HR management into a single system, facilitating efficient data management and analysis. A qualitative analysis based on four distinct case studies examines the implementation of SAP B1 and its impact on enterprises’ digital transformation efforts. In particular, the research objective is to determine how ERP systems can be analysed from a Digital Transformation perspective and how they contribute to each pillar of Digital Transformation (customer experience, business process, business model and organisational transformation). The findings provide valuable insights for practitioners to drive positive results and highlight areas that need further attention, enhancing understanding of how to implement digital strategies in practice successfully. The study’s empirical evidence can significantly benefit SMEs, the backbone of the European economy.