Jessie was born and raised in the St. Louis area. She graduated from Rockwood Summit High School in Fenton before leaving to attend Mount Holyoke College in South Hadley, Massachusetts. Before graduating, Jessie spent a year in Edinburh working as a parliamentary assistant to a member of Parliament in Scotland.

Jessie received her J.D. of the William and Mary School of Law in 2009. While attending law school she spent summers back in St. Louis as an intern at St. Louis Family Court, Juvenile Division and Interfaith Legal Services for Immigrants. Jessie returned to Missouri after her graduation and started working at Devereaux, Stokes, Nolan, Fernandez & Leonard, P.C. in the fall of 2011. Jessie is a member of the Missouri Bar and focuses her practice on plaintiff's injury litigation.