Yes, he can lose that "80 million", if the overall performance is really bad... If it will be like the acquisition of Nokia devices, when Microsoft decided to write-off over 8 billion (more than the whole deal price) as a loss, I think there is no way he would be able to convert that conditional stock award into his property... (It's also stock, so the shares better not fall...)
Net loss or no net loss, who cares (they don't count money with this kind of granularity, the stakes in that game are much higher), but if it is again a huge write-off, like with Nokia devices (which were bought before he became the CEO, so he was not responsible for that), there seems to be quite a bit protection built-in against this particular CEO being able to cash on things like that... (I don't think this protection was in place for his predecessor, who accumulated way too much personal power).
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If a competitor acquires, they might not be open to a licensing or technology deal with Microsoft, and many of them have products competing directly with Cortana and such... So a competitor would gain an advantage, and an opportunity to move forward here would probably be lost forever...
Re: Executives motivation for merging
Net loss or no net loss, who cares (they don't count money with this kind of granularity, the stakes in that game are much higher), but if it is again a huge write-off, like with Nokia devices (which were bought before he became the CEO, so he was not responsible for that), there seems to be quite a bit protection built-in against this particular CEO being able to cash on things like that... (I don't think this protection was in place for his predecessor, who accumulated way too much personal power).
***
If a competitor acquires, they might not be open to a licensing or technology deal with Microsoft, and many of them have products competing directly with Cortana and such... So a competitor would gain an advantage, and an opportunity to move forward here would probably be lost forever...