Previous studies show that digital transition brings several benefits and challenges for companies. Among those challenges, particularly for Small and Medium-sized Enterprises (SMEs), the main one is increased capacitation, from technical roles to management. Considering this, the main objective of this study is to identify the training needs and the ecosystem support in the face of the digital transition for Portuguese manufacturing SMEs. Semi-structured interviews were conducted with industry experts and company professionals in the automotive and textile sectors. It was concluded that all workers, from technical roles to middle and top management, need more digital capabilities and would benefit from training programmes. The most desired areas for training are data science, virtualisation skills, quality assurance, technical training, and soft skills. The preferred format is physical (or hybrid at most) during working hours and with theoretical training before on-the-job learning. Both industrial companies and experts believe in the value of involving external entities in the training of employees, with the three most referred entities being technology and interface centres, universities, and business associations.