Occupation. Insurance salesperson. Nationality. American. Flo is a fictional saleswoman character appearing in more than 1,000 advertisements for Progressive Insurance since 2008. Portrayed by actress and comedian Stephanie Courtney, the character has developed a fan base on social networks and has become an iconic advertising mascot. …The IFC and DEG back South African digital insurance player, Naked, in one of the largest ever African insurtech funding rounds. Naked Insurance, a South African insurtech company ...Portrayed by comedian Stephanie Courtney, the now-famous fictional salesperson strikes that perfect combination of funny and weird. Since 2008, we've been actually watching … Stephanie Courtney looks so different from her character, she's hardly ever recognized. Some commercials just stick with us, and when it comes to company mascots, it's hard to imagine a character who has become more iconic in recent years than Flo from Progressive. 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