If you don't exercise your vested options, they will automatically expire after a certain date.
The company doesn't really have any incentive to purchase your options from you, however they will likely have a clause that gives the company first right of refusal--that is, if you plan on selling any shares prior to a liquidity event, you have to first offer them to the company for FMV.
As to pre-IPO, post fund raise, your stock is typically Restricted stock units, which have clauses that prevent you from selling stock.
It's possible, with board approval to issue a special class of common stock, that can be sold to outside investors. This is usually done to allow long-term founders to get some liquidity outside a liquidity event. This typically doesn't happen for most employee's though.
In an IPO scenario, all outstanding shares convert to a single class of stock, which can be freely sold (after a lock-up period).
The company doesn't really have any incentive to purchase your options from you, however they will likely have a clause that gives the company first right of refusal--that is, if you plan on selling any shares prior to a liquidity event, you have to first offer them to the company for FMV.
As to pre-IPO, post fund raise, your stock is typically Restricted stock units, which have clauses that prevent you from selling stock.
It's possible, with board approval to issue a special class of common stock, that can be sold to outside investors. This is usually done to allow long-term founders to get some liquidity outside a liquidity event. This typically doesn't happen for most employee's though.
In an IPO scenario, all outstanding shares convert to a single class of stock, which can be freely sold (after a lock-up period).