- Beeing asked for demos when they could have tried your free tier/trial and you have decent doc (They always prefer that you waste your time then asking someone on thier side to review)
- Being used a price/feature comparison with your enterprise competitor just so they can get a better deal on their renewal (no stupid they never intended to change)
- Having to fill endless security questionnaire without being sure you can even sell to them (what you dont love filling 100+ questions at 11PM on a Friday???).
- Having to deal 3-6 months with procurement, often with one or two third party software resellers which only cares if he can make its margin (hello there CDW, no I wont lower my price 15% so you can make money)
- Receiving the money 60-90 days after the deal close while you struggle with cashflow and you had to provide the service (and receiving a call from my bank rep to see why my margin and CC is full).
I am sure I can think of more things. That is why I will absolutely charge an arm and leg to big businesses.