I think it’s fairly easy.
- Are they running an entire division or group (or more) on your product?
- Is the use case mission critical — even if niche? I.e., would the business be at risk if you went down or away?
- Is deploying your app a key initiative for your top stakeholder? Just ask if this is one of their top priorities for the year.
Then, go all in. Smother them with attention and love. Because they are probably already planning to use you for at least 3+ years off the bat. Make it a great experience, and they’ll likely not shop for another solution in those coming years.
Now by contrast, some accounts are more at risk than they seem:
- Small groups / silos at a large customer — within a larger division or organization. Just because 10 users love you at a BigCo, the CIO or others may well choose another vendor for all the other users in that division. And cancel your contract no matter how happy those 10 seats.
- A “rogue” purchase not approved by legal, procurement, etc. Sometimes a buyer will want to use your product so badly, she’ll just buy and deploy you without going through the standard internal channels and approvals. This can sound great, but it really means your application is not truly approved. That means the renewal and expansion are at risk. You haven’t truly closed the customer at an enterprise level – yet.
This latter group of customers you have to keep selling. You haven’t really won the deal yet. You have to smother them with attention, too. But you also need to keep sales on these accounts as well. They aren’t really won yet. Not really.
More here: The 10+ Year Customer | SaaStr