In 1856 Drummond commenced an engineering apprenticeship with Forrest and Barr of Glasgow. After gaining experience with his father's railway and with Peto, Brassey, and Betts, at Birkenhead, he worked under Samuel Waite Johnson at the Cowlairs (Glasgow) works of the Edinburgh and Glasgow Railway. In 1865 he became foreman erector at the Inverness workshops of the Highland Railway, under William Stroudley, and works manager in the following year. In 1875 Drummond was appointed locomotive superintendent of the North British Railway, following this, in 1882, he transferred to Caladonian Railway. In 1890 Drummond resigned from this post in order to establish an engineering works in Queensland, Australia. This project was abortive and he returned to form the Glasgow railway engineering works, where industrial locomotives were built. In 1895 he was appointed to succeed William Adams as locomotive superintendent of the London and South Western Railway.