Renowned for his elegant batting style, he played in a manner similar to the great Australian batsmen Victor Trumper, and Alan Kippax, Jackson's friend and mentor. His Test and first-class career coincided with the early playing years of Don Bradman, with whom he was often compared. Before the two departed for England as part of the 1930 Australian team, some observers considered Jackson the better batsman, capable of opening the batting or coming in down the order. Jackson's career was dogged by poor health; illness and his unfamiliarity with local conditions hampered his tour of England, only playing two of the five Test matches. Later in the year, in the series against the West Indies, Jackson was successful in the first Test in Adelaide, scoring 70 not out before a poor run of form led to his omission from the fifth Test.