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Anna Callahan has held various roles in their career, beginning with Editor and Journalist at De Anza La Voz Newspaper in 2004. Anna then served as President of De Anza College Associated Student Body in 2005. In 2008, they were an English Teacher Trainer for the United States Peace Corps. From 2011 to 2012, they were an ESL Instructor for Kaplan. Anna then worked as an Office Administrator for NetLine Corporation from 2012 to 2015. From 2015 to 2017, they were a Product Marketing Specialist for Crystal Instruments. From 2017 to 2021, they held two roles at eHealth, Inc., first as a Senior Content Specialist and then as a Content Specialist. In 2021, they were a Copywriter/Marketing Specialist for Garner Products. Currently, they are a Content Manager at e-Mission Control.

Anna Callahan received their Associate of Arts degree in Liberal Arts from De Anza College and their BA in Sociology from the University of California, Berkeley.