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Marcus Trenholm had just joined the customer success team at Shiftsmart, a company that fractionalized labor and connected gig workers with jobs and shifts. To determine whether a job was fractionalizable, Shiftsmart asked three key questions: Did the task have no substantial setup cost? Could a contractor gain expertise to the level of a full-time employee in five or fewer repetitions of the shift assignment? Was it possible to objectively measure the success of the shift? Ultimately, the questions pushed the corporate customer to fundamentally rethink and transform their approach to labor by breaking the paradigm of full-time workers performing a diverse mix of tasks requiring varying degrees of worker skill and urgency. Trenholm had been tasked with developing materials to respond to a new inquiry from RouteRunner, a southern gas station and convenience store chain, and he and his manager, Sid Singh, were reviewing an AI-generated overview of the company. Because Shiftsmart delivered its sales pitches directly to the senior management teams of its potential customers, Trenholm had to thoroughly understand the pain points of store managers and their relationship with RouteRunner’s labor model. This partially fictionalized, field-based case was developed for use at the Darden School of Business in the first-year core “Operations” course, as well as the “Operations Strategy” and “Digital Operations” electives.