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Raise your hand if you'd like to see more of Courtney beyond the aisles of Progressive. We certainly would. About Stephanie Courtney. Stephanie Courtney (born February 8, 1970) is an American comedian best known for her role as Flo in the Progressive Insurance commercial advertisements. She was born in Stony Point, New York and graduated from Binghamton University in 1992. In addition to her commercials, Courtney has appeared in supporting …Megan Fox Toys With Fans As Her Doppelganger Appears In Super Bowl Commercial. There's no hard data on how much Progressive pays out for their spokesperson. But overall, Stephanie Courtney reportedly makes about $2 million per year. That's from a combination of acting gigs, of course, though not all are as high-profile as the job with Progressive.Media Platforms Design Team. 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