High School (1994-98)
During her hign school career, Jessie was the dominant center in Minnesota, averaging 28.1 points and adding 12.7 rebounds, 3.5 assists, and 3.1 steals. She earned first team all-state Class AAAA and St. Paul Pioneer-Press All-Metro selection. As a basketball player, she collected 1,765 points, 878 rebounds, 159 assists and 155 steals in her career. She also holds the state record for most free throws in a game with 22, including 21 in a row. She was her team's MVP averaging .790 from the free throw line as a senior and redefining the center position to include agility, ball handling and passing. As a junior, she averaged 22 points and 10 rebounds as a junior. She also played on the state 16&under Tartan-North AAU team with Badger teammate Tamara Moore scoring 25 points per game. In addition to basketball, she was a three-time all-conference selection and an all-state player in volleyball and track. Jessie signed with the Wisconsin Badgers, becoming a part of Coach Jane Albright's highly ranked 1998 recruiting class.

Freshman Year (1998-99)
Jessie was named the 1999 Big Ten Freshman of the Year and a third team member of the national all-College Freshmen team by the Women's Basketball News Service, she was the only Big Ten player to make the 15-person roster. She earned second team all-Conference honors by a vote of the media, and was honorable mention in the coaches ballot. She came off the bench the first five games of the season to score double figures for the Badgers before joining the starting roster for the remaining 26 games. She was the Badgers second-leading scorer with 14.3 points and tied LaTonya Sims for rebounding honors with 6.7. She was the first UW frosh to score over 400 points as she reset the UW freshmen scoring mark with 459 points as well as tying the rebound mark with 214. She set the UW career field goal percentage mark and ranked second in the Big Ten hitting .572 (182-318). She set the UW frosh single game scoring record with 34 points vs. Ohio State (February 12, 2000) and had 14 rebounds vs. Michigan. She had six double-double games in her first BadgerBall campaign. Jessie was described as a gifted, strong, mobile post player with great range and an accurate eye. She was rated number two in the year's frosh class, behind Tamara Moore, but became a dominant starter, acing out senior Amy Wiersma from the starting line-up.