A framing question; What does (meaningful) collaboration look like in action? led to the search for and identification of a polycontext, a site where advanced collaborative activity is intelligible. This research aims to explore how the epistemic foundations of learning and design theory can adapt to collaborative approaches to organizing, learning and leadership as the macro-economic transition of digital transformation proceeds. Through embedded ethnographic engagement within a learning organization facilitating group-oriented, design-led collaborative learning experiences, a case study investigates multiple sites within a global organizational network whose distinctive methodology and culture provides a setting emblematic of frontier digital economic activity. The organizationâ€™s activity generates environments which notionally act as boundary sites where negotiation of epistemic difference is necessitated, consequently distinctive forms of expertise in brokerage and perspective-taking arise to support dynamic coordination, presenting a distinct take on group-oriented learning. Comprising interacting investigation of communities of facilitators and learning designers tasked to equip learners with distinctive forms of integrative expertise, with the objective of forming individuals adept at rapid orientation to contingent circumstances achieved by collaborative organizing. In parallel, investigating narratives of an organizationâ€™s formation led to grounded theory about how collaborative activity is enabled by shared reframing practices. Consequently, the organization anticipates and reshapes the field it operates within, the research discusses scalar effects of learning communities on industry work practices. The inquiry interrogates design-led learning and expertise formation apt for transformative activity within and beyond the digital economy. Exploring how methodological innovations within collaborative learning organizations are enacted and scaled, primary perspectives on design-led, group-oriented learning are evaluated alongside relevant secondary theoretic perspectives on collaborative organizing, learning and leading. The study synthesizes contributions that point to expansions of existing learning paradigms and anticipates how collaborative learning by design intervenes with the schematic assumptions at work in individuals, communities and fields. Observational insight, systematic analysis and theoretical evaluation are applied to problematize assumptions underlying social theory to anticipate generational expansions to the design methods field which responds to inadequacies in planning and organizing approaches applied by design. The research attempts to habituate understanding from outside design methods to better equip an explanatory understanding of contemporary design-led learning and expertise formation occurring in modern professional structures, especially in the creative industries. Together, the research investigates how learners navigate challenges of organizing, learning and leading into unseen territories.