Really helpful, thank you! I have learned some of these mistakes by trial and error - chasing way too big of a deal for way too long and wasting lots of resources

The MEDDIC framework is another good resource for any founders selling B2B: https://www.salesforce.com/ca/blog/an-introduction-to-the-me...

Rule one of sales - are you talking to someone who can actually authorise the purchase? There’s a reason why cold callers ask kids if their mum or dad is available.

At the bottom:

> In complex sales there are multiple product/market fits – Users, Buyers, etc. — each with different criteria

This is definitely something that you need to know, if it applies. And if it does, you should definitely not assume that the people in charge of deciding whether to renew are the same as the ones that decide to buy!

And while you are at it, you should be looking for other users at that organization. Call it "getting more value from your subscription" or whatever, but the more groups/departments you can get to use your product (even if not heavily), the harder it is for the money people to pull the plug. When the users aren't the people paying and the people paying aren't the ones using it, all sorts of complex dynamics come into play.

> By asking the customer to sign a fully cancelable purchase order we excluded “least likely to close prospects”

Sounds like those "free" trials where you have to provide a credit card...

this was wonderfully insightful, and ties into a lot of the best advice i've heard but never understood. If you've got excited users from a demo, isn't that all you need? Nope!