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Dan Flagler has a long and impressive work history. Dan began their career in 1990 at Verizon, where they worked as a Senior Manager. In 2017, they went self-employed as a Free Agent, and in 2018 they began working as the Director of Business Development - Americas at Smartiply, Inc. Dan has since retired from Verizon but continues to volunteer for the Chesapeake Region Accessible Boating organization.

Dan Flagler attended Vanderbilt University from 1983 to 1987, where they earned a Bachelor of Arts (B.A.) degree in Economics/Business Administration with a major/minor.