How is a sustained labor pool of transnational workers formed and transformed over time? While globalized labor circuits are often assumed, we still lack long-term systematic analysis of how they form and develop over time. Tracing diversified deployment trajectories against the backdrop of a labor-brokerage state (Guevarra 2009; Rodriguez 2010) and the transnationalization of work and family life (Parreñas 2001, 2005), this dissertation aims to advance theorizing on how a global labor force is produced, and how new cohorts of transnational workers are reproduced for global deployment. Tracking global labor from the supply-side, social scientists often draw on the emblematic case of Filipino workers—"the most globalized workforce on the planet" (Rodriguez 2010)— to explain transnational labor expansion as a self-perpetuating process. Yet, by limiting analysis to migration pathways only, scholars only predict rising numbers, overlooking the ways transnational labor-capital circuits vary and develop over time. Taking stock of over 40-years of "labor export," this intergenerational ethnography examines the formation of a global workforce beyond labor migration. In particular, I examine the co-constitutive rise of overseas and outsourced work from the vantage point of transnational worker families, suggesting that a global workforce is also historically (re)produced through the very families that bear, sustain, and socialize these workers.To do so, I follow transnational worker families across multiple locations, and gather work histories of members from various generations. Mapping out succession and spread, as one generation follows another into the labor force, I seek to link analysis of a migratory workforce and an outsourced generation. More broadly, these families reveal how emergent and enduring modes for harnessing workers as global labor historically develop, alongside rigid state regimes that still block these persons from freely moving across borders.