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In this paper we propose an automated strategy to assess participation in a multi-mode math discourse environment called Virtual Math Teams with Geogrebra (VMTwG). A holistic participation clustering algorithm is applied through the lens of activity theory. Our activity theory-informed algorithm is a step toward accelerating heuristic approaches to assessing collaborative work in synchronous technology mediated environments like VMTwG. Our Exploratory findings provide an example of a novel, time-efficient, valid, and reliable participatory learning assessment tool for teachers in computer mediated learning environments. Scaling online learning with a combination of computation and theory is the overall goal of the work this paper is situated within.