There's a pricing death valley in between "can be trivially expensed" and "needs to Go Through Purchasing"; there is a huge step function in the cost for you,

There's a pricing death valley in between "can be trivially expensed" and "needs to Go Through Purchasing"; there is a huge step function in the cost for you, the vendor, to sell into that enterprise that occurs right at that cutoff. "What costs? I sell bits over the internet, my marginal costs are zero!" I mean the cost of either your time managing an enterprise sales cycle yourself or hiring somebody to do it so you can actually work on your product, times many many potential clients (because most will fall out of the sales funnel, so you need to have lots in flight to get some in the door by the end of the month). It can be untenable to price a product anywhere between $500/mo (or whatever the cutoff is) and $20k/y.