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Penny Post-Freeman's work experience includes serving as an Office Administrator and Client Service Representative at Savant Capital Management since October 2010. Prior to that, they worked as a Branch Manager's Assistant at Morgan Stanley Smith Barney from October 2006 to September 2010. Before joining Morgan Stanley, Penny worked as a Registered Associate at Smith Barney from June 2005 to October 2006.

Penny Post-Freeman attended Illinois Central College from 1981 to 1982, though no degree or field of study information is available. Additionally, they hold a certification as a Registered Paraplanner, with no specified institution or date of obtaining.