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Ryan Sayers has worked in a variety of roles since 2004. Ryan began their career as a Real Estate Sales at Realty Executives Integrity in 2004. In 2006, they moved to Lexus of Brookfield as a Vehicle Technology Specialist. From 2013 to 2020, they worked at Toyota of Brookfield in three different roles, including Sales Consultant, Finance Manager, and Sales Consultant. Currently, they are a Sales Representative at Badger ToyotaLift.

Ryan Sayers attended UW-Stout from 2001 to 2002 and Arrowhead High School from 1997 to 2001. In September 2020, they obtained a certification in Asking Great Sales Questions from LinkedIn.