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Digital Forum: Jetblack’s Jennifer Fleiss on Conversational Disruption

Jennifer Fleiss, who helped kick-start the rental revolution by cofounding Rent the Runway, is on to her next disruptor — the Walmart Inc.-backed Jetblack. And while the conversational commerce company, which helps consumers buy just about anything via text, uses the latest technology, it’s based on a nearly antique version of customer service that’s ready for a digital-age resurgence. Fleiss, who leads Jetblack as chief executive officer and cofounder, traced retail history back to the mom-and-pop shops consumers used to rely on. They had a limited selection, but the shopkeeper could be a trusted resource when it came to recommendations. As national retailers such as Sears and Woolworth, and later mass retailers, including Walmart and Target, established themselves, product selection grew and stores moved closer to consumers, but those personalized recommendations from the local shopkeeper were lost. “More of the work was put on the consumer,” Fleiss said. “People in those stores don’t know about you as an individual as much.” That was only amplified in the “Age of Amazon,” where e-commerce has made an endless array of products available at one’s fingertips. “All of a sudden, I spent three hours searching for the perfect area rug, it’s not a great use of time,” Fleiss said.

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