[1] In 1979 a friend introduced Shepherd to Franco Belgiorno-Nettis, who offered him a job at the infrastructure company Transfield Services in North Sydney.
[4] At Transfield, Shepherd's first big project was the Sydney Harbour Tunnel, which was an early example of public–private partnership in Australia.
[1][10] As Chair of the Giants, he and other board members set key performance indicators for both the football and business side of the team.
[11] In June 2012 he was made an officer of the Order of Australia for services to business, particularly infrastructure development, the arts and sport.
[13][14] He was chairman of the WestConnex Delivery Authority from its establishment in November 2013, resigning in October 2015 when the organisation was merged into the Sydney Motorway Corporation.