AI is rapidly changing work and education. With AI@NEX, Swisscom has ventured into new territory: learners were not only trained, but also actively involved in the strategic transformation field of AI. The author examines the conditions under which they work in a self-organized manner, develop skills, and simultaneously create added value—and how these findings can support the expansion of ICT apprenticeships. The results show that self-organization succeeds when learners are legitimized from the outset, are given responsibility and trust, and can act on open-ended problems. Under such conditions, they quickly develop prototypes, initiate collaborations, and experience self-efficacy. The work makes two contributions: learners can become active agents of organizational transformation, and the insights gained are transferable to other organizations.