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Tim O'Shaughnessy has extensive experience in various leadership roles. Tim began their career at America Online as a Product Manager from June 2004 to January 2006. Tim then joined Revolution Health Group in January 2006 as the Consumer Products Lead, responsible for overseeing the consumer product management organization. In August 2007, Tim co-founded LivingSocial.com and served as its CEO until 2014. After leaving LivingSocial.com, they joined Graham Holdings as President in November 2014.

Tim O'Shaughnessy obtained a Bachelor of Science in Business Administration (BSBA) degree with a focus on Marketing and Information Systems (IS) from Georgetown University. Tim attended the university from 2000 to 2004.