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Dylan Schleicher's work experience begins in 1998, when they worked as a Production Manager at Signs Now until August 2000. Dylan then joined Outpost Natural Foods as an Assistant Manager in Customer Service from August 2000 until November 2002. In 2003, Dylan became the Editorial & Creative Director at Porchlight Book Company, a position they held until 2021. Currently, Dylan serves as the Marketing & Editorial Director at Porchlight Book Company.

Dylan Schleicher had a brief stint at the School of the Art Institute of Chicago in 1998, focusing on the study of art. However, no degree was obtained during this time.