Ask HN: What's difficult about selling to enterprises?

Length of sales cycle is a biggie. You have to stick through it for months, sometimes even years, in order to get the result at the end.

There now can be a lot more dancing around security, so you might expect to work through gargantuan spreadsheets or documents answering odd, often poorly thought-out questions about how you handle security in hundreds of places/scenarios in your organization. Once you've answered these someone might come on-site and ask you to show evidence. Then they'll want to confirm more details. A lot of patience is needed.

For one they want your company to be around in 5 years time so their spend isn't thrown away.