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Jennifer Courtney (sister) Stephanie Courtney (born February 8, 1970) [1] is an American actress and comedian, best known for playing the advertising character Flo in television and radio commercials for Progressive Corporation beginning in 2008.In fact, the human face, voice and bearing that constitute “Flo” are associated far more strongly with Progressive than with the 53-year-old woman who provides them: …Now, more than a decade since her character's beginning as a lowly cashier, Courtney's ad-libbing insurance skills and shining smile only scratch the surface of her story. Born in …In fact, Progressive created a “Flo” chatbot to enable customers to interact with Flo on Facebook Messenger, as well as other channels, to help customers with basic insurance questions. Now, Flo’s voice is being added to the chatbot, creating an even more personal experience for customers who adore the personable lady in the white apron. 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