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Robb Stottlemyer started their work experience as a Teacher/Coach at The Benjamin School in 1995, and continued this role at The Steward School from 1996 to 1999. Robb then transitioned into the financial industry, working as a Financial Representative at Northwestern Mutual from 1999 to 2004 and as an Investment Consultant at SunTrust Investment Services from 2004 to 2006. Robb then worked as an Associate Wealth Management Advisor at Executive Benefits Strategies from 2006 to 2010, before becoming a Senior Marketing Representative at Aaron Advantage Agency from 2010 to 2011. Currently, they serve as a Sales Vice President at Capitas Financial, starting in 2011.

Robb Stottlemyer completed their Bachelor of Arts degree in Communications & Rhetoric from the University of Pittsburgh, where they studied from 1989 to 1993. Following this, they pursued a Master's degree in Teaching, specializing in Education, at the same institution from 1993 to 1995.