For those interested the a16z podcast has a 22minute episode entitled "SaaS Go-to-Upmarket".

A couple of my takeaways:
It's easier to move upmarket than down.
How to think about free vs paid trials - people feel your product is of more value if they're paying for it
Why so many founders underprice - they focus on the cost for them to make the software as opposed to the cost it saves the business

The third point in particular is relevant to a company I've followed for awhile now. Brilliant idea, great competitive advantage etc but they don't charge enough for their product and the business has stalled as a result.