Established development practice seeks to first identify effective interventions and then scale them up. Significant scholarly attention (and not insignificant funding) is devoted to identifying effective interventions; yet comparatively little attention is given to the question of scale. Taking the case of digital market platforms in Nairobi’s “Silicon Savannah” and leveraging multiple methods within a full-cycle research design, this article argues that how interventions scale shapes development outcomes at a population level. While impact evaluations suggest that digital platforms can serve as instruments of economic inclusion for individual entrepreneurs, I show how, as such platforms scale, institutional pressures shape platform design in ways that prioritize engagement with large-scale, often male, entrepreneurs and marginalize small-scale, often women, entrepreneurs. Thus, ironically, benefits become distributed in ways that entrench existing gender and organizational inequalities. In attending to this paradox, I develop the theoretical and methodological scaffolding to shift scholarly attention beyond the marginal effects of development interventions towards a system-level analysis of (technology) interventions as they scale over time. This article contributes to studies of economic inclusion, technology and development, and emerging platform economies in the Global South.