Originally from Wiggins, Mississippi, Coach Jessica Olson graduated from Stone High School in 1999 where she was a four year letterman. She also held a top five state ranking during her years of USTA junior competition. After graduating high school, Coach Olson attended Mississippi Gulf Coast Community College on academic and tennis scholarships. She lettered both years while there, competing at the number one singles and doubles positions and earning an ITA ranking as high as 34 in singles and 13 in doubles for the NJCAA.
Coach Olson transferred to the University of Southern Mississippi in Hattiesburg, Mississippi, on a full tennis scholarship in 2001. She lettered two years, playing positions four, five, and six in singles and number three doubles as well as competing in the Conference USA NCAA tournament during her time there. Coach Olson assisted Head Women's Tennis Coach Randy Rowley during her final semesters at Southern Miss while completing her bachelor's degree in English.
After graduating in 2003, Coach Olson was first named the Men's and Women's Tennis Coach at Pearl River Community College for the 2004-2005 school year. Now in her sixth year with the Wildcats and the Lady Wildcats Tennis Teams, Coach Olson has continued to improve the programs. The institution played host to the MACJC State Tournament for the second year in a row in the spring of 2009 with the Wildcats finishing fifth and Coach Olson being voted men's team Coach of the Year by her peers. Pearl River also hosted the 2009 Wilson/ITA Southern Championships in the fall. In addition to coaching, Coach Olson is also an Intermediate English Instructor at Pearl River. She continues to live in the Hattiesburg area and commutes to the Poplarville campus.
Outside of collegiate competition, Coach Olson has been involved in tennis instruction such as clinics or private lessons throughout the past twelve years. She has been an Assistant Director and counselor of the Nike Tennis Camp hosted by the University of Southern Mississippi for the past three years, and has also been a counselor at an Adidas Tennis Camp held at The Hun School in Princeton, New Jersey.