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Kyle Cobban has a diverse work experience in the fields of art and design. Starting in 2010, they worked as an Artist at Threadless until 2016. During this time, they also worked as a Graphic Designer at Anchor Watch from 2014 to 2015. In 2010, they joined Nathan Hale Elementary School as a Visual Art Teacher and held this position until 2013. Kyle then transitioned to Back of The Yards IB High School, where they worked as a Visual Arts Teacher from 2013 to 2022. In 2016, they briefly worked as a Graphic Designer at QWerks. In 2021, they became an Artist at All Star Press Chicago until 2022. Currently, they hold the position of Art Director at Rocket Money (formerly Truebill) starting from July 2022.

Kyle Cobban started their education at the American Academy of Art in 2006, where they studied Illustration. Kyle then transferred to Illinois State University from 2007 to 2010, where they pursued a Bachelor of Science degree in Visual Arts - Teacher Education. In terms of additional certifications, they obtained a Diploma Program Visual Arts Category 1 Training from the International Baccalaureate in 2014 and a Diploma Program Visual Arts Category 2 Training in a later year. Kyle also achieved National Board Certification in Art - Early Adolescence through Young Adulthood from the National Board for Professional Teaching Standards in December 2019.