U.S. welfare policy researchers are increasingly considering the role of low-wage job conditions as they seek a deeper understanding of the process by which welfare recipients “churn” in and out of employment. This work, drawing on perspectives from sociology, industrial relations, and management studies, builds on more dominant scholarship on workers’ individual-level characteristics—for example, personal barriers to employment such as having young children, mental or physical illness, and lack of transportation. Incorporating organizational and other contextual approaches to the study of employment at the front lines of the labor market, researchers have noted that workers in similar low-wage and low-skill jobs face very different working conditions within and across firms, net of workers’ human and social capital qualifications and often within the same local labor market. That is to say, organizations—in this case, workplaces—matter. The paper on which this article is based built on this line of scholarship, reporting on the results of a study that involved in-depth interviews with operators of 15 full-service restaurants. The purpose was to investigate how organizational and other contextual factors corresponded with the quality of waitstaff jobs, including their compensation and access to work hours. I found that job quality varied by three major structural attributes of the restaurants, including whether they were urban, suburban, or rural; their staff size; and their status as independently owned versus chain-affiliated. This result points to the constraining role that these structural factors have over employers’ discretion to set compensation, staffing, and scheduling. Equally notable, I observed that waitstaff jobs were paid and scheduled differently across establishments that were structurally similar. This variation suggests that even when sharing major structural characteristics, restaurants choose a range of strategies to manage labor expenses, some “higher road” (meaning practices whose benefits extend beyond profits to include workers and sometimes the community) and others “lower road.” Each of these scenarios has implications for the economic vulnerability of waiters and potentially other minimum wage workers.