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Andrew Kennedy has had a diverse work experience in various industries. Most recently, they worked as the Director of Sales at Kalepa, where they focused on improving commercial insurance underwriting through AI-powered technology. Prior to that, they held the position of Strategic Account Director at Dealpath. Andrew also has experience at WeWork, where they served as the Global Client Partner and later as the Enterprise Account Director. Before joining WeWork, they worked as a Strategic Account Executive at Mark43 and as an Enterprise Account Executive at Grovo. Andrew also has entrepreneurial experience as the Founder of Vintage Inc. In addition, Andrew worked as the Director of Sales and Strategic Initiatives at Savored, Inc., which was later acquired by Groupon. Earlier in their career, they held roles at Guggenheim Partners, UBS, and Bear Stearns, where they gained valuable experience in financial services.

Andrew Kennedy attended Phillips Exeter Academy from an unspecified start year until 2000. After completing their studies there, they went on to the University of Virginia's McIntire School of Commerce where they earned a Bachelor of Science degree in Finance and Management in 2004.