Jessie grew up in Tiburon, California, just outside of San Francisco, and went to boarding school at Groton School in Massachusetts. There, she sang in the school choir and a cappella group, was a third form Prefect, and played field hockey and lacrosse, captaining the lacrosse team in her senior year.

She then attended Yale University, completing a double major in English and History. She joined the all-women a cappella group Something Extra and played club sports. She participated in the life of her residential college as a College Aide, earning the Lesser/Jackson Award given to a senior who has contributed to the life of the college. Prior to teaching at St. Andrew’s, Jessie taught at a public charter school in San Francisco with Teach For America, where she taught 10th grade English.

At St. Andrew’s, Jessie teaches English and coaches lacrosse and JV field hockey.