Shipley was born and raised in Australia, attended Epping Boys High School in New South Wales and learned to play baseball from his father, Barry.

[3] Shipley homered in his first collegiate at-bat and, as of 2022, held Alabama's single-game record for runs scored, with six in a 1984 game against Georgia Southern.

In 2003, Shipley followed former Padres executives Larry Lucchino and Theo Epstein to the Boston Red Sox, where he began as special assistant to the general manager, player development and international scouting.

[6] However, weeks after Epstein departed the Red Sox for the Chicago Cubs in October 2011, Shipley was dismissed in an overhaul of the Boston front office under the team's new general manager, Ben Cherington.

[8][9] As of 2022[update], he is still part of the Diamondbacks front office, assisting "the Baseball Operations Department in international and special assignment scouting, evaluating the D-backs' farm system and serving as an advisor to the GM.