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Jenna Weiss-Berman has an extensive work experience in the podcasting industry. Jenna currently holds the role of Executive Vice President and Head of Podcasts at Audacy, Inc. Since 2016, they have been the Co-Founder and Co-CEO of Pineapple Street Media. Before that, they worked as the Head of Audio at BuzzFeed and as a Contributing Producer at WNYC Radio. Jenna has also held roles at NPR, The Moth, McSweeney's, and StoryCorps, contributing to various podcast production and management positions.

Jenna Weiss-Berman attended Oberlin College from 2001 to 2005, where they obtained a Bachelor's degree in Politics. In 2012, they also participated in the Transom Story Workshop, although no specific degree or field of study information is given.