Software producing organizations face the challenges of changing demands, rapidly evolving technology, and a dynamic ecosystem in which their products and services need to operate. These challenges hinder software organizations being sustainable. The 5th International Workshop on Software-Intensive Business (IWSiB) brought researchers and practitioners together to discuss contributions within the emerging field of sustainable software businesses. The workshop was hosted by the 44th International Conference for Software Engineering. Birgit Penzenstadler’s keynote on software-intensive business supporting resilience and sustainability for people, sparked the interest of the participating 30 researchers that continued to discuss 12 submissions.