At the beginning of her journalism career, Jackson started working at the WBOC-TV in towns of Salisbury, Maryland and Dover, Delaware in 2006, until she departed for the WFSB in cities of New Haven, Connecticut and Hartford, Connecticut during the year 2008. In 2012, Hallie’s career led her to the Hearst Corporation, where she was the reporter for their 26 stations from Washington, D.C.