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Drew Orenstein has a diverse work experience. In 2010, they worked as the Director of Marketing at CraneKahn LLC. From 2013 to 2014, they served as a Coordinator at Newmark Grubb Knight Frank. In 2014, they established their own company, Intelligent Design, where they worked as the Founder and Managing Member. In 2017, Drew took on multiple roles at Universal Standard Housing, including Chief Executive Officer and Founder/Managing Member. At Impact Housing, they currently hold the position of Chief Executive Officer starting from November 2020.

Drew Orenstein attended the University of Wisconsin-Madison from 2006 to 2010, where they earned their Bachelor's Degree in International Economics and Chinese. In 2010, they also briefly studied Chinese Language and Literature at Nankai University. In 2009, they had a short-term experience at Beijing University of Posts and Telecommunications, focusing on China.