Who should I sent my Letter of Intent to?

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Diocletian

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I'm waitlisted at a small state school that I've applied to (I'm OOS). This is the only school I've even been interviewed at, so I really need this. I drafted a letter of intent and am planning to mail a hard copy to them instead of email, but I don't know whom to send it to. My options are:

1) The Assistant Dean, who has always been my first point of contact throughout the application cycle

2) The Dean of the medical school, who I've never talked to but whom I'm sure is heavily involved with the final decision making

Which option is best? I want this letter to be seen by the highest levels of the school, but I don't know if it's customary to jump straight to the Dean himself.

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Send it to the person that you have been in contact with, preferably by e-mail.
 
What about sending it to both? Again, preferably by email. Both figures hold a significant place to you and possibly to deciding on your acceptance.
 
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Another thought jumped to mind. I'm pretty sure that at most medical schools, the dean is WAY above the level of med student admissions. Schools of medicine are major undertakings with thousands of employees, and the dean is like the CEO.

The highest I would go is someone like an "Associate Dean for Admissions" or "Chair of the Committee on Admissions." Even still, I think it is best to e-mail it to your point of contact. They will make sure it is added to your file and seen by the appropriate people. Going outside/above this system could pay off if you are particularly compelling or charismatic, but it could also backfire by wasting someone's time or annoying them.
 
I'm waitlisted at a small state school that I've applied to (I'm OOS). This is the only school I've even been interviewed at, so I really need this. I drafted a letter of intent and am planning to mail a hard copy to them instead of email, but I don't know whom to send it to. My options are:

1) The Assistant Dean, who has always been my first point of contact throughout the application cycle

2) The Dean of the medical school, who I've never talked to but whom I'm sure is heavily involved with the final decision making

Which option is best? I want this letter to be seen by the highest levels of the school, but I don't know if it's customary to jump straight to the Dean himself.
There is no advantage, when on the waitlist (holding no other acceptances) to sending anything before May 15th. Even after April 1st the school will know that you are coming if accepted because they can see that you are holding no other acceptances. There is no need to send anything to anyone. If you feel compelled, wait at least until after May 15th.

You will only annoy the dean of admissions by going over his head to the dean.
 
Office of Admissions, really, and have them add it to your file.
 
Assistant Dean because you've already established contact
 
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