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Dale Sherrow has a diverse work experience, starting in 2005 with Butterfield & Robinson where they served as a Sales Lead and Trip Designer, managing cross-functional teams and handling operations and logistics in various regions. From 2012 to 2014, they worked as a Business Development Manager at Butterfield & Robinson. In 2014, they became the CEO of Hawkeye Sourcing and also started working as the Business Development Director for North America at Casino Global Sourcing, where they developed strategies for attracting and retaining customers. In 2011, they served as a Scout Manager at Yelp, managing freelance scouts and overseeing the creation of yelp.dk. From 2008 to 2010, they worked as a Tour and Budget Manager at 3D Management. Dale also has experience as a Business and NGO Development Volunteer for the United States Peace Corps from 2007 to 2008.

Dale Sherrow completed their B.A. in International Studies from the University of Washington from 2001 to 2004. Dale then pursued further education and earned an MBA in Business from Copenhagen Business School, studying there from 2010 to 2011.