Hailing from Bhavnagar in Gujarat, Sheldon Jackson played junior cricket in Mumbai. He was first spotted at Kolkata Knight Riders' selection trials by Joydeep Mukherjee, the former Bengal player, and was signed by the franchise in 2009. After being on the fringes of selection for his state team Saurashtra for three years, he made his debut in December 2011.

In the 2012-13 Ranji Trophy season, he made four fifties and three hundreds, including back-to-back tons in the quarter-final and semi-final against Karnataka and Punjab respectively, to help Saurashtra qualify for the final for the first time. The same year, he broke into the India A team for the series against West Indies A at home in October 2013.In 2015-16, he was part of Saurashtra's second charge towards a Ranji Trophy title. In the Irani Cup that followed, his unbeaten 59 helped Rest of India pull off the third-highest successful chase in Indian first-class cricket.

Jackson is multidimensional: Apart from being a reliable batsman and an excellent fielder, he also keeps wickets for Saurashtra in the limited-overs competitions. In the longer format, however, the presence of Sagar Jogiyani has freed up that responsibility. During the off season, Jackson is a regular in Chennai's club cricket scene, turning up for Chemplast in the first-division league.