Henry was the founder of the Pierrepoint family dynasty. He entered the profession of executioner at the age of 27 after boldly writing letters to the Home Secretary expressing his ambition to become a hangman. He had been inspired after reading about the appointment of another executioner, James Berry, and the carrying out of his first job in London. For Henry, the position of executioner presented the opportunity for travel, something that the young Pierrepoint desired from an early age.

After a period of disappointment and misunderstanding he eventually received training at Newgate Prison in London and entered the profession in 1901. He first served as assistant to the then Official Executioner, James Billington, and carried on as principal, taking part in over one hundred executions.

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