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Jennifer Steidley has held a variety of executive roles since 2005. Starting with Elliott Brainard Designs, they served as Executive Assistant to the CEO. Jennifer then moved to SharePoint360 in 2010, where they held the same role. In 2012, they joined Ampush as Executive Assistant, followed by a contract role as Executive Assistant at Ticketfly in 2013. Jennifer then worked as Executive Assistant to the CEO at University Games and Clever Inc., before joining Boosted, Inc. in 2017 as Executive Assistant to the Exec Team. In 2018, they joined Skip as Head of HR and People, Chief Of Staff, and Executive Assistant to the Exec Team. Currently, they are Executive Operations at ClassDojo, a role they have held since 2022.

Jennifer Steidley began their educational journey at Mammoth High School, where they graduated with a Diploma in 2000. Jennifer then attended the University of California, Los Angeles, earning a B.A in History and English in 2005. Lastly, they attended San Diego State University, where they earned an M.S in Criminology in 2011.