While internet technologies may support an emergent ‘wisdom of the crowd’ and new enhanced forms of political engagement, iterative design of technology is needed to better support our collective intelligence and collective action into the future. Future iterative designs need to include a synthesis of political philosophy, education, and technology design that supports the emergence of a new, higher-order wisdom of the crowd, specifically, a form of team-based system science intelligence that is matched to the complexity of the societal problems we face. Building upon the seminal work of John Warfield, we propose Applied Social Science as a new synthesis in this regard. Warfield argued for a form of applied systems science that incorporates basic science into a technology-supported science of design, complexity, and action, and he developed a specific methodology to support systems level thinking and action planning in problem solving teams. While it is possible to embed Warfield’s methodology within the World Wide Web, we argue that this is best achieved in the context of a new approach to collective intelligence design and a new politics of system change that upholds freedom as non-domination as a principle of dialogic engagement in democratic educational and political environments. We also suggest the import of design-based research (DBR) from educational science as a methodological approach to iteratively designing and evaluating infrastructures that support new forms of democratic political engagement on the World Wide Web.