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Jennie Gilbert's work experience includes founding RedChirp in 2020 and Retailer Web Services in 2006. At Retailer Web Services, they played a significant role in growing the company and authored a book titled "11 Surprising Things. . ." in 2015. Jennie Gilbert also worked as a book author for RE:MARKET in 2017, where they provided guidance on digital marketing strategies for independent retailers.

Jennie Gilbert completed their education at Arizona State University from 2001 to 2005, where they earned a Bachelor of Music degree in Music Therapy. Before attending Arizona State University, they attended Clarkson University from 2000 to 2001, where their field of study was Physics, but they did not obtain a degree.