I know that you can negotiate a signing bonus to make up for bonuses or stock options you're leaving on the table by leaving a company, but can you negotiate a signing bonus for un-vested options in a privately held company? If so, how do you know what to ask for? I have about 2000 shares vesting in late October but the company mentioned a start date in early September. The strike price is like $5 and the current valuation for the 2k shares is like $40k. Company is probably 3+ yrs from IPO.

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I mean you can try in theory, but the new org can say no. Depends if they have the budget and are willing to entertain.

A friend of mine was a VP at Mastercard and had almost 150k of unvested shares but my current company only gave her 40k signing bonus even after she showed proof.

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This, in a nutshell. It's not standard practice to take your existing vested interests into consideration, but you can make them aware of them and say it's a factor in your decision. If you have the upper hand because they really want you, they may bite, but they may not.

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