This study provides a critical appraisal of intermediaries in demand-driven workforce development. In San Francisco East Bay, an emerging set of workforce intermediaries -- here called the "Skills Brokers" -- recently take issue in alleged Skills Gaps to create a cross-sector reform agenda. They seek to connect the supply and demand for STEM skills to mediate between the booming technology industries and educational crises. Against the backdrop of structural education-industry interconnections, however, the report suggests a shift in focus. It is argued that the Skills Brokers are valuable in facilitating boundary-crossing collaboration, but their orientation towards employer demands may perpetuate educational inequities while downplaying employer responsibilities. An altered focus on supporting upward-mobility pathways requires a more proactive role by Skills Brokers that scrutinizes and shapes employer demands.