Following education at Elm House School in Sittingbourne, he was admitted as a solicitor in 1872. He practised in that town and in Greenwich and London. He entered politics when he was elected to represent Greenwich on the first in January 1889.
He was re-elected in 1892.
On the council he took a particular interest in progressing the construction of the Blackwall Tunnel. Jackson contested the as the Liberal Party"s candidate at Greenwich, standing against the sitting Conservative Member of Parliament Lord Hugh Cecil.
Jackson failed to be elected, with Cecil retaining the seat by a majority of nearly 2,000 votes. In 1900 the vestry was abolished and the County of London was divided into twenty-eight metropolitan boroughs, with the first elections to the new borough councils held 1 November 1900.
Jackson was elected to as a Progressive Party councillor, representing the South Ward.
He was mayor of Greenwich in 1902–1903. At the general election of 1906 Jackson again stood at Greenwich in opposition to Lord Hugh Cecil. The Conservative vote was split between Cecil, who advocated free trade and Ion Hamilton Benn who stood as an advocate of Tariff Reform.
Cecil finished a poor third.
Jackson only served one term in parliament, and was defeated by Benn at the next election in January 1910. Jackson resumed his legal practice.
He eventually retired to Blackheath, where he died in June 1938, aged 88. Following a funeral at Street Alfege Church, Greenwich, he was buried in Shooters Hill Cemetery.
28th United Kingdom Parliament]
He was a member of the majority Progressive Party on the council, which was allied to the parliamentary Liberal Party. He lost his county council seat in 1895 to a member of the Conservative-backed Moderate Party, largely due to the intervention of an Independent Labour Party candidate. Jackson was a member of the Greenwich Vestry and Board of Works.