I’ve successfully done exactly this.
Except in order to get there, we had to spend 3-4 years selling cheap $29/mo self-serve plans at volume to iron out all of the kinks in the product and UX. Only after that were we able to go upmarket selling $40-90k/yr contracts.
It all boils down to the fact that customers paying $20k/yr or more have extremely high expectations across the board. It’s extremely difficult to just pop into a completely new market with a brand new product untested by anyone, and expect large companies to trust and buy from you.