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Duncan Rollason has diverse work experience, beginning in 2007 as a Board Member for Writer's Block Ink. From 2007 to 2008, they also served as the Educational Outreach/ Public Relations Coordinator at Connecticut College. Rollason then moved on to positions at various organizations in the field of marketing. Duncan worked as an International Outreach Assistant, Legislative and Outreach Coordinator, and Policy Manager at Global Health Council from 2008 to 2011. From 2011 to 2016, they held multiple roles at Vermont Hard Cider Company, including Trade and Event Marketing Manager, Event Logistics Coordinator, and Cellar Staff. Duncan then worked as Trade Marketing Manager for Pabst Brewing Company from 2016 to 2018. Rollason joined Vermont Cider Company again in 2018 as a Marketing Manager before progressing to roles such as E-Commerce Director, Brand Director, and currently as the Marketing Director. Additionally, they own and manages several commercial and residential properties through Rollason Properties LLC. Overall, Rollason has a strong background in marketing, event management, and property management.

Duncan Rollason obtained their Bachelor of Arts (BA) degree in Psychology/Sociology from Connecticut College, where they studied from 2003 to 2007. In 2005 and 2006, they also completed a certificate program in Multiculturalism and Social Change at the University of Cape Town.