[MehdiEG]

"1. Someone in the executives actually likes the site the way it is."

That one is probably the main reason why companies stick with awful-looking websites. I'll never cease to be amazed at how many people have no design sense or eye whatsoever and genuinely cannot see the difference between an absolutely horrendous-looking logo or page and a well designed one.

In fact, not only can they not see the difference but I often see them preferring the godawful version over the well designed one. There's a reason why every home-made flyer uses Word's multi-colored 3D fonts and wordart - a lot of people genuinely think that they look absolutely amazing :)

[paolomaffei]

if they also sell to people that think those flyers are amazing then is it really a problem for them?

[piotr_krzyzek]

100% agree with this statement, though my followup question to that is: do we have to stick with mediocrity? Or can/should better design/quality outpace and outperform the current drivel?

[MehdiEG]

No, it's not a problem per se, why? It's just one of the reason why crappy design still abound, which was the OP's question.