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Madelyn Flinn began their work experience as an Investment Banking Analyst at VRA Partners, LLC from July 2015 to September 2016. Madelyn then worked as a Corporate Strategy & Business Development Analyst at Toyota Tsusho America from September 2016 to October 2017. In 2018, they joined S'well as a Financial Analyst from February to July, and then as a Senior Financial Analyst from August to December. From 2018 to 2021, Madelyn worked at Zola.com, starting as a Senior Financial Analyst and progressing to the role of Associate Chief of Staff. Their most recent role at Zola.com is Senior Manager and Chief of Staff, which they held from March 2021 to March 2022. Currently, Madelyn Flinn serves as the Director of Strategic Finance at Zola.com, starting in March 2022.

Madelyn Flinn attended the University of Virginia from 2011 to 2015, where they studied at the McIntire School of Commerce with concentrations in Finance and Management. In 2014, they also participated in a semester abroad program at the University of Bath, focusing on Finance and Management. Prior to their university education, they attended The Collegiate School from 2005 to 2011.