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Master scheduling governs how time, talent, and space are allocated, yet scholarship rarely attends to the people who build those schedules. This qualitative study analyzes schedulers’ goals, processes, and the impact of implementing innovative AI-driven scheduling tools. Sixteen scheduling leads across four U.S. secondary systems were interviewed after adopting Timely, an AI-optimization scheduling software. Deductive coding revealed (1) persistent trade-offs among legally mandated, remedial, and advanced student groups; (2) idiosyncratic, historically inherited training; and (3) sizable time-savings that shifted leaders from clerical work to strategic thinking. Findings illuminate how AI can repurpose scarce educator time toward equity-focused design, with implications for policy, preparation, and research agendas.