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Jamie Siegel has a diverse work experience spanning various industries. They began their career at 33 Club as a Marketing Associate from June 2009 to October 2010. They then worked as a Marketing Design Intern at The Nature Conservancy from January 2011 to September 2011. Following that, they served as a PR/Media Manager at Karyn's from October 2011 to November 2012. From November 2012 to November 2014, Jamie worked as a Brand Communications Manager at GoPicnic. They then joined Leo Burnett as a Communications Specialist from December 2014 to June 2015.

In 2015, Jamie transitioned to Enjoy Life Foods as a Marketing Manager, focusing on Social & Consumer Engagement, from September 2015 to January 2019. They later became the Senior Relationship Marketing Manager, specializing in Email, Social, and CRM, from February 2019 to October 2019.

Currently, Jamie Siegel holds the position of Director, eCRM & Digital Marketing, Membership at WBEZ, a division of Chicago Public Media. They assumed this role in October 2019 and were subsequently promoted to the role of Director, Digital Engagement Strategy in July 2022. No end dates have been specified for their current roles.

Jamie Siegel attended Smith College from 2004 to 2008, where they earned a Bachelor of Arts degree in Art History and French Language. In 2007, Jamie also studied at the University of St Andrews, focusing on the History of Art. Prior to college, Jamie attended New Trier from 2000 to 2004. In 2010, Jamie enrolled at DePaul University, majoring in Art, Media, and Design.