With recent and rapid advances in areas such as online games, embedded systems and Internet of Things, the traditional notion of what constitutes a system, as well as how a system is typically developed, is fundamentally changing. Instead of systems that are specified upfront, and for which there are pre-defined purposes and tasks, we are increasingly experiencing a situation in which interconnectivity and emergent configurations of systems allow dynamic system capabilities that evolve and adjust over time. Regarded as the new digital business paradigm, these types of systems offer fundamentally new ways for software development companies in their service-and value creation. At the same time, they present challenges in these organizations. In this paper, and based on multiple case study research in three different domains, we identify emergent system characteristics that pose new challenges on software development. We present a model that outlines the transition from traditional development towards 'Human/System Synergistic Development' (HuSySD), in which software development is a joint effort between software development teams and intelligent systems.