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Jackson DeLisle has a diverse work experience spanning from 2010 to the present. In 2010, they began as a Junior Entrepreneur at Forward Progress, Inc. Jackson then worked as a Social Media Intern at Forward Progress, Inc. from 2012 to 2015. In 2014, they worked as a Stockboy at Welch's Stop and Shop. From 2016 onwards, they held various roles at both Forward Progress, Inc. and Social Jack, including Business Development, Production Manager, Speaker, Trainer, and Coach. In 2019, they worked as an Audio Technician at Lake Central Theatre Company. In 2020, Jackson co-founded Untied Entertainment and served as a Co-Founder & Content Creator. Jackson also hosted The Untied Podcast and started their own podcast called Jackson Street Podcast. In 2021, they began hosting Windy City Joe's Podcast.

Jackson DeLisle's education history begins with their high school diploma, which they obtained from Lake Central High School between 2012 and 2016. After completing their high school education, Jackson attended Purdue University Northwest from 2016 to 2018, focusing on communication with a specialization in advertising. During this time, they also enrolled in the Improv Olympic - i.O. program in Chicago, where they pursued a degree in comedy writing. In 2019, Jackson joined the Second City Training Center in Chicago to study comedy and improv. Additionally, Jackson has obtained certifications such as Inbound Certified, Frictionless Sales Certified, and HubSpot Sales Software Certification from HubSpot in July 2022.