[ddebernardy]

Stepping in and highlighting the problem before it happens come to mind.

If you anticipated that such complexity was involved in data entry at any point, putting upper management in front of their responsibility might have helped, i.e. "how do you think dev morale will look like if they need to do data entry for weeks just so we can make a few more quick sales?"

[IgorPartola]

I think this was my biggest mistake. I underestimated the problem and while I explained it to the upper management I did not push it hard enough for them to make it a number one priority.