Jessica Casciola attended undergraduate at New College of Florida in Sarasota, Florida. She concentrated in Economics and Political Science and wrote an undergraduate thesis on the Conflict in Iraq and how it influenced the stock market. She pursued her Juris Doctor at the University of Florida and graduated with her J.D. in 2007. While in law school, she participated in Moot Court and was an editor in the International Law Journal. After graduating, she began working at the Office of the Public Defender in Gainesville, Florida. She then went on to the Office of the Public Defender in Bradenton, Florida and practiced there for nine years. While in the Bradenton office, Ms. Casciola worked in misdemeanors, felonies, appeals, and, prior to her departure, was a felony division chief. She left the Office of the Public Defender to become an assistant federal defender in Panama City, Florida. She was the sole assistant federal defender in that office and was employed at that Office until coming to the Tampa Division in 2019.

Ms. Casciola is also a Captain in the United States Army JAG Corps. As a JAG Corps officer, Ms. Casciola has represented soldiers in administrative actions to separate them from the US Army. She was also mobilized to be the legal advisor to the 2019 Department of Defense Warrior Games.