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When Purva Gupta emigrated to the U.S. from India and did some online shopping here, she found herself surprisingly frustrated. Why was it so hard to seek out the precise form of dress she was searching for? Considering it is likely to be an immigrant problem resulting from a language or cultural barrier, she did some hefty local research to “test her hypothesis.” But after speaking with greater than 1,000 women, she confirmed there was definitely a disconnect between how consumers experienced and perceived products, and the way brands and retailers described such products. This compelled her to create an AI-driven solution that bridges the merchant-consumer gap. WWD caught up with Gupta to debate Lily AI, which she cofounded with chief...