He rose from traffic clerk to telegraphist, studied shorthand at night school, and became stenographer to the general manager.

[3][4][5] Webb resigned from the United States Railroad Administration in 1920 to become vice president and general manager of the St. Louis Southwestern Railway until May 1921.

[6] In 1922, when he started his appointment in Adelaide, Webb considered that by applying business operating principles he would be able to get the South Australian Railways on a footing where they would give a minimum return of 6 per cent on the investment.

He did not foresee however, the impacts of the Great Depression and the growth of ownership of motor cars, nor was he fully aware of the millstone of the hundreds of miles of developmental lines, with their unpredictable seasonal agricultural traffic.

His most important changes to working methods occurred in 1924–26: the train control organisation[8] was introduced in 1924, high-capacity bogie freight cars[9] in 1925, and large-power locomotives[10][11][12] in 1926.

[13] Webb was noted for his abilities to enthuse his staff, particularly his senior officers, so that the whole system was imbued with the spirit to serve, to persevere and to deliver the goods.

After Webb's departure in May 1930, his administrative reforms were dismantled and the old hierarchy was reinstated,[3] although the South Australian Railways were in a better position than most to meet the huge logistical demands of World War II.

[note 2] On returning to Dallas, Webb, by then very well off financially, served as a member of the city council and did a lot of work for charities.