Jessie Lee Dickson was a graduate of Bennett High School May 28, 1930. She later matriculated Bennett College in 1934 with a Bachelor of Arts Degree. She honed her musical ability while attending both high school and undergraduate school at Bennett College. She became an integral part of the original Bennett College Quartette.
During the early growth of Bennett College much funding was needed and a clientele needed to be cultivated. This involved informing different aspects of the community the needs and goals of the newly formed women's college. The Quartette was one such vehicle that was used for that cultivation. The original Quartette consisted of Grace Coulbourne, Jessie Lee Dickson, Nannie Wright, and Maidie Ruth Gamble. The Quartette accompanied Dr. David Dallas Jones on many speaking engagements before constituents. During the years of 1928-1934 the Quartette represented Bennett College in song both locally and nationally. Travelling to such places as New York, Pennsylvania, Virginia, and neighboring cities in North Carolina. Entertaining such groups as the Women's Home Missionary Society, and many Methodist Institutions. The Quartette was the public face of what the Bennett College women represented at that time.