Mistakes are to be learned from
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Not mapping out and getting to know all the stakeholders in a deal. And after the deal
This is a skill you need to learn quickly in the enterprise. The person that contacts you often is just one of many stakeholders in the purchase. Don’t assume whomever you are currently talking to you is the buyer, or even in the end, the decisionmaker. Every deal is at renewal risk if you don’t get to know, and map out, all the key stakeholders.
Not being responsive to every key concern.
I remember my CTO once arguing with a Fortune 500 company on a “security” concern they had which really made no sense. It literally made no sense, and in fact their app did the same thing. But that didn’t matter. They were concerned. That meant we had to be concerned. You can’t do everything. But you can be responsive to every key, top concern.
Not visiting enough customers in person.
I never lost a customer I visited in person. But the ones I didn’t, were the ones that silently churned. Even / often when the usage was high. More here: I Never Lost a Customer I Actually Visited
Not hiring a full-time RFP person
If you are going to do a lot of RFPs, they need an owner. They are too much work to just dump on a product person, success person, sales leader, etc.
Not hiring a full-time Chief Security & Compliance Offer
Hiring a CSO way early if you are truly going enterprise. It just makes the customers so much more comfortable. And then security audits, reviews, etc. go so much faster and easier.