Jesse began his formal ballet training at 16 and graduated from Walnut Hill School for the Arts. He attended summer programs at Boston Ballet, Alonzo King's Lines Ballet and Ballet Austin. In 2000, having completed his freshman year at the University of Chicago, he returned to dance. After a year with Ballet Austin he joined Richmond Ballet where he danced for eight years, performing works by John Butler, Jessica Lang, Val Caniparoli, William Soleau, Mauricio Wainrot and Colin Conner. Jesse joined Hubbard Street Dance Chicago in August 2010.