Digital transformation is one of the main challenges that SMEs face nowadays. Nevertheless, to a great extent, they lack the necessary capacities and skills to introduce and apply technologies that can support digitalization. As a design science approach, researchers from different European countries have carried out the collaborative research project VOIL to collect and scientifically develop resources and tools to support SMEs in building digital skills. In the context of this project, a tool is developed to assess the digital maturity of SMEs. Moreover, a learning journey based on the use of simulators is proposed together with a minimal viable prototype integrating all developed tools to provide a comprehensive learning environment. Lessons learned from the application of said learning online environment in experimental settings are also shared. The project results contribute to the research that has been carried out within the scope of life long learning, proposing the aggregation of pedagogical strategies that allow self-guided learning in the workplace.