Although work schedulers serve an organizational role influencing decisions about balancing conflicting stakeholder interests over schedules and staffing, scheduling has primarily been described as an objective activity or individual job characteristic. The authors use the lens of job crafting to examine how schedulers in 26 health care facilities enact their roles as they “fill holes” to schedule workers. Qualitative analysis of interview data suggests that schedulers expand their formal scope and influence to meet their interpretations of how to manage stakeholders (employers, workers, and patients). The authors analyze variations in the extent of job crafting (cognitive, physical, relational) to broaden role repertoires. They find evidence that some schedulers engage in rule-bound interpretation to avoid role expansion. They also identify four types of schedulers: enforcers, patient-focused schedulers, employee-focused schedulers, and balancers. The article adds to the job-crafting literature by showing that job crafting is conducted not only to create meaningful work but also to manage conflicting demands and to mediate among the competing labor interests of workers, clients, and employers.