Once qualified, he moved to Bristol to find work, and became active in the National Union of Operative Boot and Shoe Riveters and Finishers.
[1] In 1887, Sheppard joined the Social Democratic Federation, and he also served as honorary secretary of the Bristol Socialist Society.
In 1893, he was elected to Bristol City Council as an independent labour representative for St Pauls, and was re-elected in 1904, serving until his death.
He subsequently left the SDF and became prominent in the local Labour Party, standing unsuccessfully for Bristol East at the January 1910 general election.
He served on the tribunal for conscientious objectors during World War II and remained politically active until shortly before his death, age of 94.