Growing up near the home ground of Balmain District Cricket Club, Jackson joined the club in his mid-teens where he quickly came to the attention of the captain, Test bowler Arthur Mailey. The Labor politician "Doc" Evatt, a noted benefactor of young cricketers, helped Jackson's career by purchasing suitable cricket equipment for him. At the age of 15 years and one month, he made his first grade début for Balmain; cricket historian David Frith believes that Jackson is the youngest cricketer to play at this level.