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Jessie Weingartner has a diverse work experience in the education and retail sectors. Starting in 2009, Jessie worked as a Special Education Teacher at Teach for America for two years. Following that, from 2011 to 2012, Jessie served as a Response to Intervention Coordinator K-4 at Teach for America New Orleans. In 2012, Jessie joined Intelligentsia Coffee & Tea as a Project Manager/Assistant to CEO for one year, and then transitioned to become the Assistant Director of Retail Operations from 2013 onwards. Finally, in 2014, Jessie joined The Noble Network as an Assistant Principal.

Jessie Weingartner attended Duke University from 2007 to 2009, where they obtained a Bachelor of Arts (B.A.) degree in International Studies/Romance Languages. In the same year, 2007, Jessie also enrolled at New York University, however, no information is provided regarding the degree and field of study completed at this institution.