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Gary Cowan started their work experience as an Associate Consultant at LEK-Alcar in 1989. Gary then worked as a Senior Director at RealNetworks from 1999 to 2003. From 2003 to 2005, they held various roles at MSN Search, including Director of MSN Search and Group Product Manager for Windows. In 2005, they joined Amazon.com as a Director of Amazon Search Traffic. From 2007 to 2016, they worked at Datasphere Technologies, Inc. as the SVP of Product and Marketing, where they were responsible for product management, marketing, and business operations. In 2016, they became the COO of Peach Inc., where they focused on driving company growth and success across various functions. Gary then worked at Amazon from 2018 to 2022 as the Director of EU Automated Marketing, leading customer acquisition and engagement strategies across the EU markets. Currently, they hold the position of Vice President at Permira since 2022.

Gary Cowan attended Harvard Business School from 1997 to 1999, where they earned their MBA degree with a focus on Business. Additionally, during the same period, they also studied at Harvard University and obtained another MBA degree, specializing in Business.