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This field-based case recounts the story of two executives facing a critical decision at Walmart-backed, India-based Flipkart Online Services Private Limited (Flipkart), an expanding e-Commerce company. After easily onboarding the company's first 200 million customers, they must decide how best to attract and retain Flipkart's next cohort, who are generally younger, have less disposable income, are more comfortable speaking native Indian languages, and have very different shopping patterns. The executives are considering two initiatives: an AI-powered voice feature and video-led shopping experiments. Which of the two can be justified both strategically and financially for the long term, as well as sustain itself without company subsidization? Can Flipkart do both? If it can, should it? At the University of Virginia Darden School of Business, this case is taught in a first- and second-year MBA elective called 'Digital Marketing'. It would also be suitable in a module covering the AI-enabled customer experience or digital ROI.