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R. Casey Winter has held various positions in the technology and hospitality industries since 2003. From 2003 to 2005, they were the Corporate Catering Manager for Specialty's Cafe & Bakery. From 2005 to 2007, they were a Sales Engineer and Senior Launch Coordinator for Pay By Touch/Solidus Networks. From 2008 to 2015, they were the National Sales Director and Business Development for YapStone. From 2015 to 2018, they were the VP of Sales and Business Development for Aptexx, Inc. and the Sales Manager for Digital Solutions for OSG Billing Services. Since 2018, they have been the VP of Business Development and Partnerships for Obligo.

R. Casey Winter attended the University of San Francisco from 1999 to 2003, where they earned a Bachelor's degree in Political Science and Government. In 2002, they also attended Richmond, The American International University in London, where they earned a Certificate for Cross-Cultural Management & Communication in International Business.