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Jennifer Caldeira has worked in the customer service industry since 2007. Jennifer began their career at Zazzle as a Content Manager. In 2013, they joined Stitch Fix as a Stylist and Refix Operating Lead. In 2020, they moved to Flip Fit as a Customer Experience employee. Most recently, in 2021, they joined FashionPass as a Member Concierge Team Lead.

Jennifer Caldeira attended Santa Clara High School from 1993 to 1997, and is currently attending Cuesta College.