Following the lead of other developing regions, sub-Saharan Africa has experienced an expansion of schooling, accompanied by delays in marriage and lower fertility. Theoretically, these trends stand to foster women‟s employment and reduce gender inequalities at the family, labor market, and national levels. A variety of cogent arguments about why African countries could reap socioeconomic dividends from current socio-demographic transformations exist. But the evidence has been spotty, reflecting a number of limitations in theory, data, research design and substantive focus. The goal of this research is to address some of these limitations using a longitudinal approach and triangulating evidence from multiple sources and countries. Building on recent changes within countries and the diversity of national experiences, I attempt a large-scale empirical analysis to document the size and sources of changes in women‟s labor force participation in sub-Saharan Africa between 1991 and 2005. To this end, I adopt an innovative empirical strategy: 1) I use nationally representative and comparative Demographic and Health Surveys (DHS) data on 21 African countries to build a large-scale longitudinal household level dataset of over 404,000 cases. 2) Next, I classify the countries into employment regimes based on country development stage to facilitate comparison. 3) I then examine how gender and national contexts affect this relationship by complementing the DHS dataset with qualitative data and retrospective event history data for an in-depth contextual analysis. Finally and importantly, I examine the theoretical logic and cumulative life course effects of schooling, marriage and fertility by triangulating three methodological principles in micro-macro framework. The overall results are insightful. With respect to schooling and inconsistent with the human capital perspective, educated women have generally not reaped the anticipated benefits, especially in the formal labor market, even as they are more likely to work compared to their non-literate peers. In contrast, the fertility findings are mixed. Fertility decline is likely to yield economic and social returns ultimately, thus challenging the role incompatibility thesis in about 29 percent of the study countries. The evidence on marriage is the strongest. It is driving the changes, whether gains or reversals, in women‟s formal employment in 95 percent of the sampled countries, providing little support for economic specialization thesis. The above study insights reveal several policy directions for SSA. While women‟s schooling is important in its own right, with additional health and social gains, a comprehensive rather than unilateral policy focus on formal education should be pursued. In the same vein, a one-sided emphasis on reduced fertility and delayed marriage without providing women opportunities to access and retain secure and stable jobs can be pointless. Instead, context-specific marriage-related policies focusing on couples and emphasizing healthy and appropriate marriage timing, sustained across the life course should be the new direction. Life-long marital relations that are mutually beneficial to both partners would improve women‟s socioeconomic status with the latter, in turn, being the more sustainable route to low fertility and poverty reduction. In terms of research, these transition effects unfold in a multiphasic and stage-dependent manner, underscoring the importance of multi-method triangulation in a longitudinal framework