A bailiff is a manager, overseer or custodian – a legal officer to whom some degree of authority or jurisdiction is given. Bailiffs are of various kinds and their offices and duties vary greatly.
Bailiff's notice on boarded-up premises, London, 2015
Ontario provincial bailiff shoulder flash
In Anglo-Saxon England, the reeve was a senior official with local responsibilities under the Crown, such as the chief magistrate of a town or district. After the Norman Conquest, it was an office held by a man of lower rank, appointed as manager of a manor and overseer of the peasants. In this later role, historian H. R. Loyn observes, "he is the earliest English specialist in estate management."
The lord's reeve overseeing serfs at harvest time
Oswald the Reeve in "The Reeve's Tale" by Geoffrey Chaucer