Digitalization is amongst the various challenges that European Small and Medium-Sized Enterprises (SMEs) face in today’s climate. A major number of SMEs, report that they do not possess basic digital skills, resulting in a positive link between digital skill levels and turnover growth. Digital uptake is indeed consistently lower in smaller firms across countries, and diffusion gaps are relatively constant across firm size classes (OECD, 2021[14]). SMEs deal with several difficulties towards developing an online presence, they have a lack of awareness about the benefits and opportunities available related to digital resources, they are not familiar with digital platforms implementation, they do not have the solid knowledge to understand and assess digitalization transformation, digital formations, and online tools and platforms, and thus, they do not engage in Industry 4.0. Digital transformation is vital for SMEs as it can present unique opportunities. However, in order to fully exploit these opportunities, SMEs must invest in training themselves and developing their digital skills in order to overcome existing digital skills gaps and mismatches, take advantage of an even wider range of opportunities brought about by ongoing advances in digital technologies, platforms, applications, and devices. In addition to this established situation, a new reality has come, namely the coronavirus pandemic (COVID-19) introducing changes in the employment reality that will last. Teleworking became a very common job alternative and it is a surprise that the former resistance which existed to this digital change, suddenly evaporates. Additionally, SMEs and self- enterprises are vital to the European economy, making up 99% of Europe’s businesses and accounting for two-thirds of total employment (OECD 2017a). Despite its strength and innovativeness, Europe is at risk to fall behind in the global digital race. There is a shocking lack of digitally skilled workforce across the continent, resulting in an estimated digital skills gap of as many as 1,000,000 employees. SMEs in the digital economy, are coming to realize that digital skills are vital for employees in the digital era, and they have to follow suit, or risk being left out of digital supply chains. The DIGITUP project aims to develop both an innovative, accessible training course, a serious game and further assessment tools and piloting activities that will practically facilitate VET teachers and educators to train SMEs’ managers and self-entrepreneurs for being the future managers- holders of cutting edge digital skills, who will be able to achieve the digital transformation of their work and businesses based on Industry 4.0 framework and BIC technologies.