Those titles are merely symbolic and don't come with 'real' responsibility, because the actual management is done by other people.
I don't really want to become the 'leader' anyway, from roleplaying perspective this means your character is "retired" from adventuring and is supposed to be focussed on his new job.
I think it's a lot better to focus on stories and career-paths that are less dependable.
Leading a mercenary group, or becoming an entrepreneur or a pirate/thief etc... that's all good because you can quit doing those things whenever you want and it's still believable.
As far as some other established guilds go, it doesn't make any sense that a young adventurer takes over after saving the guilds ass a few times over the course of a month or two.
I would be perfectly happy to receive a highly respected status with some additional benefits while not being at the top of the ladder. Preferably still being able to do some (randomly generated) shores.
Being able to become the leader of every organisation you join is just ridiculous and unnecessary, especially when you don't have a choice.