Webb began his career in 1851 as a pupil of Francis Trevithick, at London & North Western Railway, Crewe Works. In 1859 he was made chief draughtsman and then in 1861 he was appointed chief assistant to John Ramsbottom. In 1866 he left Crewe to become the manager of the Bolton Iron & Steel Company; however, after the retirement of Ramsbottom, in 1871, Webb was appointed to the position of Chief Mechanical Engineer, at Crewe. He resigned from the position in 1904.