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Drew Baillie has a diverse work experience that spans over several companies and industries. Drew started their career as an Elementary School Teacher at Wonderland English Academy in 2008. Drew then transitioned into sales and logistics management at Coast Seafood AS from 2010 to 2015. In 2015, they joined Ekata (formerly Whitepages Pro) as an Account Executive and later held roles as an Enterprise Account Executive and Director of Strategic Accounts, Enterprise. From 2018 to 2023, Drew worked at DocuSign, progressing to positions such as Account Executive, Major Accounts, Manager, Enterprise Corporate Sales, and Regional Vice President, Enterprise Corporate Sales. Currently, they are the Regional Sales Director at Signifyd.

Drew Baillie obtained a Bachelor of Science (B.S.) degree in Psychology from the University of Washington. The degree was completed between 2003 and 2007. There is no additional information available about their education beyond this point.