Building upon the work of John Warfield past president of the International Society for Systems Sciences, this paper argues for a new synthesis of political philosophy, education, and technology design that supports the emergence of a higher-order ‘wisdom of the crowd’, specifically, a form of systems-thinking collective intelligence that is matched to the complexity of the societal problems we face. Warfield’s collective intelligence and applied systems design methodology is described along with a number of recent EU project applications. Recent educational innovations are also described, in particular, the functional integration of Warfield’s systems thinking tools with Argument Mapping tools as part of classroom education, and the development of a new systems science curriculum focused on the tools, talents, and team dynamics needed to support collective intelligence skill development and applied systems design work. While it is possible to further embed Warfield’s methodology within educational and organisational practices, and within the World Wide Web, consistent with Warfield’s view it is argued that a new politics of system change is needed that upholds freedom as non-domination as a principle of dialogic engagement in these environments. Furthermore, consistent with the principles and practices of design-based research (DBR), it is recommended that the systems sciences merge with the learning sciences to iteratively design and evaluate infrastructures that support new forms of collective intelligence and applied systems design work.