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Anna Jacobs has worked in a variety of roles in the sales and customer service industry since 2007. Anna began their career at Anthropologie as a Senior Sales, Customer Care Specialist. Anna then worked as an Art Director at G2 Direct & Digital (Grey Direct) and as a freelance Art Director at Avanti Press. In 2008, they moved to Kate's Paperie as a Retail Manager. From 2011 to 2017, Anna worked as a Sales Executive at both Haig's of Rochester and The Sam Tell Companies. During this same period, they also had a Customer Service Sales Support role at BKLYN Larder. From 2012 to 2015, Anna served as a General Manager at both Friedman's Lunch, Chelsea Market and Friedman's Herald Square. Most recently, they have been an Inside Sales Account Manager at Applied Manufacturing Technologies since 2022.

Anna Jacobs attended Michigan State University from 2000 to 2004, where they earned a Bachelor of Arts in Advertising. Anna then attended Miami Ad School (M.AD School) from 2004 to 2006, where they earned an Art Direction degree in Advertising.