This contribution provides preliminary results relating to the evaluation of a web-based platform for cultivating a sense of initiative and entrepreneurship in compulsory education. This platform is used in Finland and abroad, and it was experimented for the first time in three Italian upper secondary schools as substitute of work experience during the COVID-19 pandemic. The article presents entrepreneurship education in Europe, and it explores the educational policies related to entrepreneurship in Italy. Next, it shows the model the platform is based on, and presents this evaluative study as multiple embedded case study: Focus groups were organized in the three classes with students and teachers, who performed a SWOT analysis on the use of platform as work experience. The analyses were subsequently validated through interviews to teachers. The explorative research questions concern: the first evaluation of the web platform; the extent this platform can be used for work experience; and possible differences of the application of the platform in the three contexts. Preliminary results suggest that the use of the platform as cross curricular subject during work experience nurtures a sense of initiative and entrepreneurship taken as key competence for lifelong learning.</p>