My personal career path was Product Manager -> VP -> CEO. In the process I met a lot of VP's that weren't very good - you want to focus on what it takes to be a GOOD VP, not just a VP. It really broke down to just a few things:
1) Be a stellar product manager. Check out Ben Horowitz' "Good Product Manager/Bad Product Manager" (http://www.khoslaventures.com/pr...) for the template. Note that a good product manager has vision, recruits others, has good strategic sense, and displays good management of others.
2) Ask the hard questions, and have some answers. There's nothing I love more than a Product Manager who is acing everything about their job, but wants 20 minutes to talk to me about the big questions. What are people seeking in social technology? What are the Top 10 things that can kill our progress, and what are we doing about them? What is it that makes Groupon successful and how do we get a piece of that in our experience? Have some theories, but be open to feedback.
3) BE THE STORY. Use the product. Talk to people. Be the change you want your company to be in the industry. Recruit relentlessly, whether there is an open position or not. Practice the company pitch until you do it better than anyone, and take media training so you can deliver it effectively in a group. Always, always, always be positive and never, never, never blame the company/others for things that go wrong - just help fix it. Give credit to others any chance you get - those who really know will know the contribution you made.
4) Step up. Volunteer for the hard problems (without losing track of your current job, of course). Get used to saying this - "I'm so sure I can address this issue, I will bet my career on it". The truth is, you bet your career on every move you make. Might as well get credit for the accountability.
5) Ask for feedback. Seek out your peers, other VP's, and stakeholders and ask how you could improve. Listen and repeat back what you've heard. Come up with some ways to address your weaknesses and share them with those who gave you the feedback. Don't wait for a formal review. Let people know about your ambitions.
When I took my first VP job, I forgot to ask the question "what do you think are the areas where I could most likely fail?". When I stumbled, it was a surprise to me, but nobody else. That's where crappy VP's begin and end. I was wise enough to get back on track by asking for a lot of feedback, but it sure would have been easier if I had just assumed I know nothing on the first day and asked for help.
Remember, you don't get a VP promotion because you deserve it - you get it because they need you to execute. You can't cast the final vote on your abilities until you do. Then you will find out why VP's get paid more - it's really, really hard.
In case it wasn't clear, I almost always tell folks that the best way to the top in a start-up is to begin as a product manager. Few roles force an understanding of all the business as much as a PM, and there's a great opportunity to demonstrate leadership skills. I personally have been offered VP-level jobs and asked for a lower level job for this reason.
Start-ups are a scramble, but have about 3x the learning curve. Find a company where you adore the product/service, and jump right in. Don't worry so much about the title - people will be handing them out left and right once it hits its growth curve. You will never regret it.
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