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Peggy Kayser began their work experience in 1987 at the REALTOR(r) Association of NorthWest Chicagoland, where they served as the CEO for over twenty-four years until September 2011. From October 2011 onwards, they held the position of Chief Programs Director at the Mainstreet Organization of Realtors.

Peggy Kayser attended Columbia College Chicago from 1996 to 2002, where they earned a Bachelor of Arts (B.A.) degree in English and History.