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Jenna Gales has a wealth of work experience, beginning in 2008 with an internship at Alligator Records and Artist Management as a Public Relations Intern. Jenna then held an internship at North Iowa Area Community College in 2009 as a Marketing and Community Relations Intern, as well as a Student Blogger for Loyola University Chicago's IgNation. In 2010, Jenna held two internships at Loyola University Chicago as an Event Planning Intern and Marketing and Communications Intern, as well as a Public Relations Intern at Chicago HOPES. Jenna then worked as an Account Executive at the Chicago Sun-Times in 2011. From 2012 to 2021, Jenna worked at the Chicago Bulls in various roles, including Senior Analyst, Business Strategy and Analytics, Digital Strategist, and Digital Content Coordinator. Most recently, Jenna has been the VP of Performance and Data Strategy at FanReach since 2022.

Jenna Gales obtained their Bachelor of Arts in Public Relations and Advertising from Loyola University Chicago in 2011. In 2020, they obtained four certifications from Oracle: Eloqua Campaign Execution Master, Eloqua Marketing Creative Master, Eloqua Marketing Operations Master, and Eloqua Master.