As an undergraduate at the University of Alabama, Jessica served as President of the Student Government Association. Prior to attending law school she served with former State of Alabama Attorney General Jeff Sessions (currently United States Senator) and as director of public relations and legislative affairs for former Attorney General Bill Pryor (currently US Court of Appeals Judge, 11th Circuit). She also served as law clerk for former Tuscaloosa County Circuit Court Judge L. Scott Coogler (currently U.S. District Court Judge). She successfully managed the 2010 Luther Strange Campaign for Alabama Attorney General and later served as Chief Counsel and Deputy Attorney General in the 2011 administration of Attorney General Luther Strange.
In July 2011, Jessica became executive director of the Republican Attorneys General Association. In 2014, Jessica became the first president of the Rule of Law Defense Fund, the public policy organization created to provide a forum for Republican attorneys general to engage on issues relevant to promoting the rule of law, federalism, and freedom in a civil society.