[hkarthik]

As someone that probably comes close to fitting the bill, here are the reasons I wouldn't apply.

1. You're in NYC, where everyone is currently getting obliterated by snow. For positions like this you should hire in spring or summer if you want to attract a candidate from warmer climates.

2. You want someone who can put in the hours of a 20-something but has the experience of a 40-something. To me, that says the management team wants to hire 2-3 people for the price of one. These expectations simply aren't realistic and anyone brought in will fail in one capacity or the other.

3. The company raised or earned enough to hire you to hire for this postion. So clearly they had someone fulfilling this role but it hasn't worked out. That implies a lot of interpersonal conflict on the management team (all too common in startups).

I think if you start with hiring a VP level and focus on hiring a manager first, you will be better off. Who ever comes in should expect to promote from within and/or hire externally quickly. The management team needs to heavily involved in selling a prospective candidate on the role to alleviate any concerns about the interpersonal conflict.