This research considers the creation of resilient organizational models of urban governance to foster urban sustainability. Building on large-scale urban experimentation initiatives, we identify relevant factors in establishing urban experimentation with the help of digital platforms as a means to support such resilient organizational models. Our findings suggest that digital platforms help establish urban experimentation platforms (UXPs) as a core means to innovate towards urban sustainability. UXPs utilize digital platforms to coordinate policy measures and stimulate collective intelligence in order to reach a sustained local socio-technical transformation process. Based on these empirical findings, we use a systems lens to decompose urban experimentation into interconnected sub-systems and then describe some characteristics of their dynamic interaction. Our goal is to develop a System Dynamics model and simulations to support urban public authority decision makers in formulating and implementing policy interventions towards urban sustainability.