Get the last 409A valuation. That's the price the shares should trade at and in fact will create problems for the company if they do not.
If the CEO offered the last 409A valuation as a price, then there's little you can do if you're inclined to take an offer because the 409A is the "fair market value" of the common stock. Usually the 409A is a huge discount, like 60-80% less at the stage you've implied the company is at, under the preferred price.
Also, missing in this discussion is that the board likely has to ratify any change in ownership and the board (led by the CEO) has tremendous ability to just say no and/or dictate who and at what price can buy. All this discussion of the what the fair value of the shares might be to outside investors is somewhat irrelevant in that situation.
Yes but it can actually cause problems if the board approves a lower price than the 409a valuation. He has some leverage in that respect, especially if his sale of shares can be worked into the funding round.
If the CEO offered the last 409A valuation as a price, then there's little you can do if you're inclined to take an offer because the 409A is the "fair market value" of the common stock. Usually the 409A is a huge discount, like 60-80% less at the stage you've implied the company is at, under the preferred price.