There is a huge difference between selling software to ICs / tactical managers (directors and below) and strategic managers (VPs and above).
Simply put, employees who don't have budgeting responsibilities unconsciously compare the price of software to their own salary.
"I'm paid $100k/yr and I have like five key responsibilities. This software will help me with one of those responsibilities, so it's worth, what, $10k, maybe?"
I'm not saying that ICs and tactical managers explicitly say the above, but it's all about the feels. They have limited scope in the business and, as a result, they look at all purchases as a function of how much the company invests in THEM.
Strategic managers consider the inverse -- employees and software are each a function of the business opportunity. Show them millions of dollars in opportunity and they'll spend hundreds of thousands of dollars to achieve those goals.
If you find yourself stuck in the sub-$20k deal size, it's time to move your sale up the corporate ladder.