[vessenes]

You've got a bunch of options, depending on your interests and skills.

You could be a repository-of-lore brilliant coder / guru. Sounds like this is roughly what the CEO has carved out for you right now.

You could be CTO/Head of Engineering. You may or may not want this job or be suited to it, based on what you've said so far.

You could sink down into the organization as a (hopefully) really rich mid-level engineer and enjoy the ride.

You could do it again as a founder rather than early employee somewhere else.

I think you should figure out what would be best for you, what you want, and then see if the CEO agrees and will make it happen. At some level, if you're a few years into vesting, and the company is successful, it may not significantly change your financial outcome to stay -- you have early stage stock in a successful startup. More could be nice, but it won't change your outcome 10 or 100x, like moving to a founder role would.

Lots of good options; just don't do the west coast thing and stew on it while you write increasingly bitter tweets and blog posts. :) Today is a great day to get some clarity!

[trhway]

> At some level, if you're a few years into vesting, and the company is successful, it may not significantly change your financial outcome to stay -- you have early stage stock in a successful startup.

somewhat related question - doesn't the huge taxes on the options exercise upon leaving make that huge difference between leaving and staying? How does people manage it? Doesn't it forces you to stay until the exit?

[vessenes]

I'm sure you're right there are some tax consequences; I'm definitely not an accountant, though.

In a friendly situation if the company is in good shape, there are probably lots of options, including some sort of buyback to get enough cash for the taxes, or finding an investor who'd like the shares. If the company isn't doing as well as advertised, those possiblities are probably harder to get sorted.

[seanmcelroy]

For the US - Depends on if you're exercising and holding or exercising and selling. If you didn't get the opportunity, or forgot, to take an 83(b) election as a founder, then you've been paying income taxes as your shares vest. If you were keen on taking that 83(b) election, your tax liability is negligible on liquidation and you pay nothing until that point for usual ISO arrangements.