[fotoblur]

I see a number of posts saying that you're probably not experienced or qualified enough to hold these other positions. However, I don't think the VP of Eng, Dev Mgr, or OPS Mgr could do what you do...essentially help start and build a company from day one.

Those skills you've developed don't have much value at your current company any longer. They are most likely keeping you around for historical value and once the systems you built get replaced its over pretty quick. Take those skills elsewhere and brand yourself as someone who takes a company from 2 to n employees.

Not everyone has your skill set so learn how to market them. I'm on my second company where I was an early hire. I learned that you're way more valuable in the beginning then you are at the end. Eventually I got pushed out by management types because I held on to the notion that I helped build this company and deserved something for it. Don't wait too long to realize it.

[prostoalex]

+1, witness how the company needs changed from generalists to specialists.

The experience is probably quite frustrating since every specialist they hire is supposed to handle their aspect of specialization better than you (otherwise why hire them?) - the support manager probably has better and more complicated pipelines for support, the ops guy probably owns various issues that were put on the backburner before.

Wrong way to think about it is try to squeeze yourself into a specialist position, and then keep wondering how did things get to be so bad.

Some right ways to think about it would include addressing some areas where specialization is missing (research? next-gen architectures?) or just moving on (to a different place).

[nwatson]

The rub is:

* the OP will need to pay a lot to buy their vested options when they leave each company

* the fair market value of common stock will have probably increased so they'll also need to pay immediate income tax on every gain

* they likely won't have a market for their shares until acquisition or IPO (five to ten to never years)

* the shares they do have will be diluted 10x or more through Series A/B through F, and they won't benefit from readjusted new 4-year-vesting grants

* they'll learn a lot and profit little from serial startup monogamy

[walterbell]

Try to join when stock has low paper value, exercise the options immediately so there is no gain and no tax. Then you vest shares, rather than options, and can take them with you.

[chrissnell]

This is great advice. I will also add that if you want a leadership role, model your resume around your leadership experience at this company. You've led a team of 10 people. So say that on your resume. It was your high water mark and you don't have to tell people that you're not leading 10 today. Go out and get that leadership role if that's what you want.

[takemikazuchi]

What's the financial outlook for this career path? I've always heard bad stories about early hires dealing with a below market salary(for a while) with worthless stock options. Is this a myth? It never made sense to me since I feel an early hire should make significantly more than average, since they don't have the power/equity advantage of a founder, probably have to work long hours, and a large part of the success of the company rides on their shoulders.