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Dwight Hutchinson began their work experience in 1994 as the Guest Programs Manager for Cruise West. Dwight then moved on to the Bill and Melinda Gates Foundation in 2000, where they served as the Onsite Training Manager until 2004. In 2004, they joined WA State Ferries as the Smart Card Project Manager and later became the Terminal Operations Manager - South from 2009 to 2017. In 2017, they joined Rick Steves Europe as the Guide Services Manager, where they managed a team of field guides and oversaw the operations of European tours. Currently, they are the Operations Manager at Northwest Administrators, Inc.

Dwight Hutchinson obtained a BA with Honors in International Studies with a focus on Eastern Europe and the USSR track from the University of Washington. The duration of their education at the University is not provided.