We explore digital transformation and socio-technical systems through the perspectives of collaboration, co-generation, and domestication. Building on Morten Levin’s influential work, we discuss how digital technologies are integrated into work environments, emphasising the necessity for democratic, participatory approaches. We discuss how his ideas of collaborative, democratic practice originating in the 1990s hold up to today’s organisational challenges like digital and sustainability transitions. Are the ideas and practices still valid, or do we need to update them? We identify the grand challenges that must be met: Ensuring sustainable digital transitions and developing educated, skilled workers in digitally transformed organisations.