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Paul Chiaffredo's work experience begins in 1997 as a Professional Baseball Player in the Minor Leagues for the Toronto Blue Jays. After their baseball career, they worked as an Inside Sales representative at VistaScape Security Systems from 2003-2004. In 2004, they joined the Pittsburgh Pirates as a Professional Baseball Player in the Minor Leagues until 2006. Paul then transitioned to the tech industry and joined SecureWorks in 2007 as an Inside Sales representative until 2009. In 2011, they started working at Bomgar Corporation, where they held various roles including Enterprise Software Account Manager and Regional Sales Manager. Their tenure at Bomgar Corporation lasted until 2016. Currently, since 2017, Paul has been working at BeyondTrust, where they have held positions such as RVP of Corporate Sales, SVP of Small Mid-Enterprise Sales, and currently serves as the Senior Vice President of Americas Sales.

Paul Chiaffredo attended Leland High School from 1990 to 1994. Paul then pursued a degree in Marketing at Santa Clara University's Leavey School of Business from 1994 to 2000.