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Chieftain is the title often given to the leader of a clan, village, or even a town. Based on the example of Skogr, the role seems to be held for "life" (that is, for the entirety of one's adulthood until death or a willing abdication to a successor).
Most often, the title (and its privileges) are passed through specific familial lines from father to son (as implied in the description for the Jarl's Seal).