In an era marked by economic, financial, and health-related crises, the concept of “grand challenges” has gained prominence, signifying complex issues with global repercussions that demand innovative solutions. This chapter explores the potential of cooperative initiatives and open innovation strategies as novel approaches to addressing these challenges. Drawing on a case study of “La Scuola Open Source,” a cooperative project situated in a socially challenged context, the chapter delves into the dynamics of crowdsourcing as a strategy to navigate societal transformations. The study highlights the pivotal role played by open practices and design-driven methodologies in nurturing a profound sense of community belonging and drive a community-driven initiative to a formalized cooperative entity. The study provides valuable insights for practitioners and policymakers in the field of social innovation, particularly those striving to address pressing grand societal challenges.