Unfortunately many of these points have been learned by living them. If you are looking at an early stage company, make sure you get a true understanding of the state of the business. The longer a start up has been around, the more "scar tissue" from previous decisions, actions, and mistakes.
The 'experience' and background of the team, representations made by employees or recruiters, cash in the bank, investor/VC support, etc. are really not enough to accurately gauge an opportunity.
Everyone is selling so be sure to get to the core of the business quickly. Here's a handful of questions I suggest you get answers to before taking a position:
- Tenure of VP Sales
- Tenure of VP Marketing
- How many predecessors in each role and why aren't they there anymore
- Tenure of CEO
- How many predecessors in the role and why did they leave/why were they terminated
- Level of operational/day-to-day engagement
- Identify the last 5-10 deals closed
- What was the deal close timing including how near/far apart and where they were on the calendar
- When they entered the pipeline
- When they were forecasted to close
- Their dollar/revenue size
- The lead source & similarities in sources among them
- Implementation/activation status for these deals
The answers to these questions will tell you if you are staring at a turnaround opportunity or a growth opportunity. You can then decide what you're up for as both have their pros and cons.
Oh and get a demo. If they can't show it to you or if they do and it's not compelling, you'll have a great indication of what lies ahead.