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Blair Baldwin's work experience includes serving as the Cofounder/CEO of Boundless Rider since September 2021. Prior to this, Blair was the Head of Boston Studio at Haven Life from August 2018 to August 2021. Blair also founded and served as the General Manager of AgeUp from August 2018 to July 2021. Before that, Blair was the Co-Founder/CEO of Quilt (acquired by MassMutual) from July 2015 to August 2018. Blair also worked as the Chief Marketing Officer at Goji from February 2013 to July 2015. Additionally, Blair was the Chief Product Officer at Dailybreak from July 2011 to January 2013. Blair started their career as a Consultant at Kennedy Information from September 2002 to September 2003 and held various roles at Digitas from 2003 to 2007, including Manager, Strategy & Analysis and Senior Analyst, Strategy & Analysis. Blair was also a Principal at High Start Group from August 2009 to July 2011 and a Summer Senior Associate at Innosight in June 2008.

Blair Baldwin pursued their higher education in a chronological order. From 1998 to 2000, they attended the University of St Andrews, although the specific degree obtained is not provided. Following this, between 2000 and 2002, Baldwin enrolled at Harvard University and completed a degree in Sociology. Finally, from 2007 to 2009, they attended the Harvard Business School, where they acquired an MBA.