The compound “salesman” was originally the compound “sails-man.” To relieve the kingdom of undesirables, Tudor monarchs would have these pests “man the sails” on merchant ships. Recognizing the economic benefits of shamelessness and dishonesty, the merchants often sent these “sails-men” into towns to vend wares. While the merchant tended to other business, the sails-men would try to sell goods at the market. The possibility of receiving a five-percent commission inspired many of the men to raise the art of the sales pitch to unprecedented levels.
Incidentally, the term “fire”—as in, “Let’s fire Johnny before he is eligible for a pension”—comes from the method used by merchants to ensure that sails-men returned with the profits and unsold goods. Sails-men were branded with a mark recognized throughout Europe. People who captured and returned escaped sails-men would receive a monetary reward, and the sails-men would earn an all-expenses-paid vacation to a burning pit; in other words, the sails-men would be “fired”.
A notable early use of the terms “sails-men” and “fire” appears in Tremblestaff’s Merchantman of Florence:
When sails-men giveth me all that is due,
Their prize will be a pretty pound or two.
But mark! If runneth they away with it,
‘Tis time to light a flaming, fiery pit.
Post nigh the ashes there enmired,
“Here lie some rascals who a merchant fired.”