After a brief spell teaching at Christ's College, Finchley, for six months during 1887, Jeffrey became an assistant mathematics and science master at The Skinners' School, Royal Tunbridge Wells, whilst simultaneously studying for an Inter Bachelor of Science, with first class honours [REF].
In 1894 he took up another post, this time to become a holiday modern-languages tutor (a well paid position) to the son of Sir Thomas and Lady Glen-Coats, Thomas Glen-Coats,[REF] later to compete at the 1908 Olympics.