Yep. I've worked at a couple startups where engineering built a thing, sales was able to sell it but had to give a huge discount. The resulting economics just didn't work. But, each sale was seen on its own as a success even though the generally lost money. Often there was a discount plus some promised bespoke feature that required additional development to close the sale. There was never enough volume and often that additional engineering work never applied to another customer. Nobody wants to say "maybe this deal just isn't worth making" and move on.

In a couple of these cases, the company was ultimately sold in a fire sale. The early investors, founders, and employees got nothing. The acquisition is still celebrated as a "success", of course.