Skilled migrants are moving through global circuits in strategic sites of the global economy, bringing with them advanced expertise and knowledge. These migrants are engaging in complex and non-linear migration patterns across the life-course, yet these patterns are difficult to study empirically with existing data due to the increasing scale and dynamism of global skilled migration. This dissertation develops novel data sources that allow for new approaches to the study of skilled migration in institutional, transnational and longitudinal perspective across the life-course. These new tools are better able to capture dynamic migration flows as migrants move between countries in the transnational labor market in complex ways that standard survey data are not able to examine due to temporal and spatial issues the methodological design of many cross-sectional and national-level datasets. Drawing on quantitative analysis of employment histories of 7,177 migrants and qualitative analysis of 105 in-depth interviews, I show that overlapping institutional arrangements influence the development, flow and settlement of skilled migration. The empirical analysis centers on a comparison of Indian skilled migrants with degrees from American and Indian universities, focusing on place of education as a key driver of variation in migrant pathways and settlement behavior. Each of the three empirical chapters explore the close relationship between education, work and migration. First, I find that migration policies are simultaneously leading to convergence and differentiation between educational attainment in U.S. and Indian university systems. Further, country of education influences migrants’ occupational attainment in the country of first job and current job. Finally, employer-sponsored visas constrain the development of foreign skill and can contribute to return migration. These findings have methodological implications for studying skilled migration in transnational and longitudinal perspective. They also illuminate new concepts in migration studies, underscoring the overlapping institutional arrangements between state and non-state actors in regulating the flow and incorporation of skilled migrants.