How do I tailor a demo to the buyer's pain?

You know the goal is the buyer's real pain, not your feature list. The trouble is that tailoring takes information you do not always have when you walk in, so some demos land and some drift. That unevenness is a discovery problem as much as a demo problem. A demo only speaks to pain you have actually uncovered. When it falls flat, it is usually because you were guessing at what mattered to them instead of knowing. The fix lives before the demo starts, in the questions you ask and the notes you keep on what this particular buyer is trying to fix. Try this. Before your next demo, write down the one problem this buyer told you keeps them up at night, and open with exactly that. Build the first three minutes around their words, not your product tour. When they hear their own pain reflected back, the whole room changes.