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by cdnsteve 4177 days ago
Here are my thoughts with limited knowledge of your situation.

As employee #2, you are a technical co-founder, period. The problems you have outlined will not be solved be staying at the current company. It's apparent that the owner has chosen to keep you as 'just a dev', even though your contributions are outmatched and significant. It seems opportunity to seize more than what you could have has unfortunately passed you by.

From what you're describing in your post, it seems you're showing regret. Other people have been hired for these positions, even though you built it.

The thing is about being an early employee is that it's a blessing and a curse. Most people don't realize this but the thing is the feeling you get for being the guy that put this company where it's at today is unmatched.

The problem is that once it's built, you go into maintenance mode and it turns into a corporate machine. Everything you enjoyed and discovered during the process is now going through "procedures" and "process". The freedoms gone, other people are here now and they start getting the ears of the owner instead of you.

You feel like you own this company, you should, you built it and partied with the owner for years (guessing here). The biggest regret at this point is that you probably don't own enough (equity) or you were never made co-owner.

You have a choice, stay and give your last effort to be in the position you earned. Or leave, full well knowing that you will likely not be #2 at a successful startup again. We all know that startups getting successful is about the same as winning in the lotto. However, you could be the guy you are describing in your post, the VP of Engineering that gets hired for a startup that is starting to grow...

In either case I wish you the best of luck and as another dev can appreciate the weight of your decision.