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Jessica Conway has a diverse work experience, beginning with their role as a Military Police in the U.S. Army Reserve in 2006. Jessica worked as a Chef for Cameron Mitchell Restaurants in 2008, and then as an Assistant Manager/Bartender/Host for Sakura Japanese Steak House in the same year. In 2010, they joined the US Army as a Criminal Investigation Division, and also worked as a Front Desk Agent for Hilton Columbus Polaris in the same year. In 2011, they became a Debit Card Fraud Prevention Analyst II for JPMorgan Chase. Jessica then worked as a Vet Assistant for Heartsong Vacine Clinic in 2015, and a Dog Trainer/Pet Sitter for Companion Animal Nanny in 2016. Finally, in 2020, they became a Tinkergarden leader for Tinkergarten.

Jessica Conway's education history includes a Certification in Dog Training from Animal Behavior College from 2015 to 2016, a Bachelor of Science in Hospitality Management from The Ohio State University from 2004 to 2011, and an Associate's degree in Culinary Arts from the Columbus Culinary Institute at Bradford from 2007 to 2009.