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This case recounts the journey of Evie.ai, a Singapore-based tech start-up. Specifically, the case examines how founder Lee Jin Hian and his team developed and implemented Evie, an artificial intelligence (AI) personal assistant. There are very few teaching cases on AI and its impact on work and employment. Commercial applications of AI may promise substantial potential gains to individual and organizational productivity, but we need to be aware of their limits as well. This case introduces students to AI and how this technology can be informed by data analytics and applied to various tasks. It also offers lessons on the realities of running a start-up: students will gain a deeper understanding of tech entrepreneurship (or 'technopreneurship') from analysing the challenges and opportunities that confronted Evie.ai, and in navigating the decisions the start-up needed to make in the face of mounting competition and rapid technological shifts.