[frozenport]

Leave.

Be pragmatic: there will be other opportunities which are equally interesting and staying isn't helping. You could be CTO at a different startup. Further, you should be approximately at your zenith at the company and they should be able to provide a strong reference, if you stay dissatisfied your performance and appearance will suffer - along with your potential for future employment.

Also happiness is about the journey (career, parenting, etc). If you're not on a journey you won't be happy!

[cheriot]

He's probably got a 4 year vesting schedule and maybe a more recent evergreen grant with another 4 year vesting schedule. As intended, that's a good incentive to work on the problem before giving up.

The thing missing from the post is a description of what he wants. If it's more recognition, I bet he could talk to the founders and work something out. To them it'll be a justified and free way to keep a great engineer.

[amirmc]

> Leave.

If he's got options, they'll be vesting -- typically over a 4yr period. He's 2yrs in so if he decides to leave, then he'll lose half of them. If he's willing to do that, then he'll have to exercise what he already has vested. Does he even have the cash to do that?

It's easy to suggest that people just 'move on' but it's important to remember the context.

[dmur]

>If he's willing to do that, then he'll have to exercise what he already has vested.

Not necessarily. It depends on the terms of his or her options grant. Many companies give employees a 10 year exercise period after they leave (advocated by Sam Altman: http://blog.samaltman.com/employee-equity).

[amirmc]

> "Many companies give employees a 10 year exercise period after they leave"

I suspect many companies don't do this, as there'd be no need to advocate for it otherwise.

[jayp]

A 10-year exercise window has to be extremely rare to the order of non-existing in SV startups. Maybe it's picking up stream since the article was written and I am not aware of it. Can an employee vouch for his/her employer (company) that does this? Do more recent YC companies do this?

In fact, even Quora hadn't actually implemented a 10-year exercisable window by the time (or right before the time) Sam's article was written: see comment at https://news.ycombinator.com/item?id=7610668. Note that the article simply mentions it as an idea; not as an ongoing implementation. I wonder if it is now actually implemented at Quora.

[idunno246]

Except after 90 days ISO become NSO, so you lose tax benfits. But maybe he 83b'd them and already purchased as employee #2

[untog]

Very easy to say, but if you have significant equity (which, as employee #2, you really should) it's a lot more difficult to just step away.

"The journey" is all very well, but if that journey involves checking out for a year while you wait for a payout then so be it.

[gaius]

One company, a good friend of mine was employee #1 and I was something like employee #40. After the IPO it turned out we'd gotten the same package equity and options-wise, which is to say, not much... Being an early employee, 99.9% of the time! means getting screwed.

[chime]

> if you have significant equity (which, as employee #2, you really should)

That's the big unknown here.

If he does have significant equity (even 2.5% or more is good), then what's the problem. He gets to share the long-term benefits without any of the stressful responsibilities and can be solely devoted to doing what he's best at. If a brief mention on About Us page is all he cares about, bring it up at your next review and say that it's not about ego specifically but more about career advancement and personal growth.

If he doesn't have decent equity then he should've quit long ago and hanging around any longer isn't going to be any more satisfying. Unless he is super critical to their development (i.e. only he knows how module X works), then he could negotiate a better job title at the threat of leaving but that could be a risky and burn-bridges move.

[kasey_junk]

I'd be surprised if he has any "equity". He may have options, but that is a significantly different thing. Most onerously of course is that if he leaves he will likely have to shell out actual cash on a lottery ticket. Who knows if he can afford to do this, or if it makes sense to do this.

That is a long way of saying, under almost any reasonable scenario, whether he has significant options (vested or no) should not be the determining factor on if he should stay.

He should stay if it he enjoys the job, they are compensating him enough in real compensation to overcome his lack of enjoyment, or he doesn't have other job opportunities.

I will say, as a long term employee (though to be fair, it's not that long term) he should have the ability to more forcefully outline what he wants to continue with the company. If he doesn't, either he's fooling himself about his real value, or he is doing a poor job communicating it to the company. In either case, it's his issue.

[nwatson]

Being early employee with 3% quickly turns into burnt out employee with 0.2% after a couple of funding rounds in adverse conditions with a brand new VP engineering who doesn't have the bandwidth or interest to find out how really vital you've been and how much more you still have to contribute. No shiny options package for you. Enjoy the holiday ham and the subsidized yoga.

[andrewtbham]

Rather than checking out..... consider spending time trying to get mentored by the new managers. Think of the way Larry Page was mentored by Eric Schmidt. Also spend time reading about how to manage a large team.

Also consider... do you want to manage a large team? Or do it again from the ground up?

[frozenport]

>>involves checking out for a year

Woah, I'm not saying you shouldn't be getting paid. The trick is getting paid while you are interviewing for new positions! Just make sure your interviewing for them.