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Shawn Flanagan's work experience includes various roles at Program Brokerage Corporation and Philadelphia Insurance Companies. At Program Brokerage Corporation, they started as the New Business Development Leader in 2006 and later became the Assistant Vice President for Professional Lines in 2009. In 2014, they were promoted to Chief Sales Officer and eventually became the Senior Vice President in 2017. Prior to that, they worked at Philadelphia Insurance Companies as the Underwriting Manager for Professional Lines from 2000 to 2006.

Shawn Flanagan attended Penn State University from 1996 to 2000, where they earned a Bachelor's degree in Insurance and Business Management.