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David Armstrong's work experience begins in 1994 when they co-founded Timesoft Computersystems. David served as the Co-Founder until 1998. In 2000, they became a Launch Team Member and Director of Operations at ocean24.com until 2002. From 2002 to 2011, they worked at FTI GROUP in various roles, such as Director of Systems & E-Commerce and Founder & CEO of fly.de & drive.de. In 2007, they also served as the CEO of erf24. In 2011, Armstrong became the CEO of PDM Tourism Group and held that position until 2012. From 2013 to 2014, they served as the CEO of Congrex Switzerland. Currently, Armstrong is the CEO of HolidayPirates Group, a position they have held since 2014.

David Armstrong has participated in several educational programs and institutions. David attended the Saïd Business School at the University of Oxford, where they completed the Oxford Executive Leadership Programme. Additionally, they studied Technology Entrepreneurship at Harvard University and Business Strategy at The Wharton School. Their education history also includes a focus on Business Administration and Management, General, which they pursued at the University of Cumbria. David further expanded their knowledge in the fields of History and Political Science at the University of Maryland Global Campus. Prior to their higher education, David Armstrong attended the Gisela-Gymnasium High School in Munich, Germany.