Digital platforms increasingly mediate economic coordination, labor allocation, and decision-making. As artificial intelligence becomes embedded within these platform ecosystems, automation no longer targets only manual labor. Instead, algorithmic systems are displacing routine tasks across both low-wage entry-level work and middle-management functions. This paper argues that the emerging phase of platform-mediated automation risks hollowing out labor structures from both directions, from below through the erosion of repetitive, junior roles, and from above through the automation of supervisory coordination functions. Drawing on institutional economics, platform governance literature, and recent research on AI-enhanced learning and workforce development, the paper examines how this dual displacement creates structural vulnerability. Entry-level roles have historically functioned as apprenticeships in which workers acquire tacit knowledge and critical judgment. At the same time, experienced workers are aging out of the workforce. If platforms curtail formative occupational layers, organizations may face a shortage of workers capable of exercising contextual reasoning required to manage complex systems. The paper situates these developments within broader debates about technological unemployment, platform labor, and the political economy of capitalism. It argues that the challenge is not merely job quantity, but institutional continuity, how societies reproduce practical competence when platforms optimize for efficiency rather than formation. This study proposes a framework for evaluating platform ecosystems by their long-term effects on human capital formation and institutional resilience.