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In this paper, we introduce Compass, a chat platform where industry professionals mentor large cohorts of 30+ students with the support of novel features that enable full engagement without the typical chaos of group chat. Specifically, we conceptualize conversations as composed of not only individual messages, but also multi-person conversational units that collapse large numbers of small but related conversational exchanges into single conceptual units in the main dialogue. Doing so makes it possible to preserve a coherent linear flow of conversation while also supporting non-linear conversational exchanges that can be concisely summarized computationally and built on in the main conversation. We report on design lessons learned over a year of small real-world studies culminating in a final deployment in which 2 industry professionals successfully mentored 30+ students over a 10-week period. 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