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Jenny Cobb has a diverse work experience spanning over a decade. Jenny began their career at Verona Area School District and Madison Metropolitan School District as a Substitute Teacher from 2007 to 2008. In 2006, they worked as an Assistant Manager at Cheeseburger in Paradise until 2009. From 2009 to 2014, they held multiple roles at Madison Media Institute, including Financial Aid Administrator and eventually Associate Director of Financial Aid. In 2014, they transitioned to ASCAP as a Licensing Associate. Their most recent role was at Eventbrite, where they started as a Customer Experience Associate in 2015 and eventually became an Associate Manager - Customer Experience in April 2019. In this role, they were responsible for customer support through various channels and also took on tasks such as quality feedback measurement, mentoring, and training.

Jenny Cobb obtained a Bachelor of Science degree in Elementary Education and Teaching from Edgewood College, where they studied from 2004 to 2006. Prior to that, they pursued Elementary Education and Teaching at the University of Wisconsin-Madison from 2001 to 2004.