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Lewis Matthiessen Wheelwright has a diverse work experience starting as an International Program Coordinator at Centers for Interamerican Studies from November 2008 to January 2010. Lewis Matthiessen then worked as a Manager of Operations at Pacific Food Solutions from January 2010 to February 2012, where they developed a Natural Marinate Enhancement technology and handled various responsibilities including equipment maintenance, record keeping, raw material management, and customer communication. Following this, they served as an Ambulance Driver at Camden First Aid Association from November 2011 to May 2012. Lewis Matthiessen also worked as a Snowboard Instructor at Camden Snow Bowl from December 2011 to February 2013. From April 2012 to April 2016, they held the role of Management/Sales/Lead Mechanic at Sidecountry Sports, a bike and ski shop in Midcoast Maine, where they performed tasks such as inventory management, customer relations, and sales. Currently, they hold the position of Senior Vice President at Legacy Properties Sotheby's International Realty, starting from March 2014 onward.

Lewis Matthiessen Wheelwright attended Syracuse University - Maxwell School from 2004 to 2008, where they earned a degree in International Relations with a focus on International Political Economy & Latin America. In 2008, they briefly studied at the University of Chile in Santiago, Chile, obtaining a Bachelor of Science (BS) degree in International Relations and Affairs. Additionally, from 2006 to 2008, Lewis studied at the Center for Interamerican Studies (CEDEI) in Cuenca, Ecuador, specializing in Spanish Language and International Relations.