Jessie debated for Harrison High School for four years, and was a team captain as a junior and senior. She earned a career total of 12 TOC bids, reached the final rounds of Greenhill, Bronx, and the Glenbrooks, won Isidore Newman and UPenn, and was top speaker at Durham, Isidore Newman, and Princeton. She reached semifinals at Yale and Durham, quarterfinals at NCFL Nationals, and elimination rounds at the TOC as well.