Jobe was educated at Kostka Hall preparatory school before studying at Xavier College in Melbourne.
Watson's talents at Australian rules football became obvious and his expectations of becoming an AFL player due to his legendary father were high with him looking very much like his father. Before the 2002 AFL Draft, Essendon expressed interest in using the father-son rule to obtain him.
Much taller than his father, Jobe was initially groomed as a key forward for Essendon. However he took time to find his feet in the side. His poor kicking by AFL standards drew criticism, however his creativity as a playmaker and ability to accurately find targets by hand made him more suited to the midfield at Essendon. Additionally, early in his career, his ballooning weight was criticized in the media after he weighed in at over 90 kilograms.
Soft tissue injuries interrupted his progression in both the 2003 and 2004 seasons, and his form did not improve during 2005.
Several times during his career, including his first game his father Tim had called games involving Jobe as a commentator on television, and raised eyebrows for his open criticisms of his son's playing at times, however his father revealed that his comments were only aimed at constructive criticisms.
However Watson worked extremely hard after 2005 to get leaner to meet the rigours of the AFL midfield and following his promotion to the AFL midfield, his form improved substantially.
He capped off the 2006 season with 2nd place in the Crichton Medal voting.