eg: if my booking is wrong, they will cover the cost and compensate me. It would sort of just come down to buying premium travel insurance for everyone that uses it. And insurance for anything else they do. It has to be one of two things - they either believe the risks are worth it (so then there should be a financial model that can absorb the cost of insurance to do it), or in fact, the risks are too great. At some point, if they keep offering the tech on a "use at your own risk" basis, they are implicitly communicating that they themselves think the risks are too great - so YOU shouldn't trust it either.
That would be nice, but it's the wrong angle. The reason people like real secretaries is not because somebody is compensated when things go wrong. It's because things don't go wrong. I don't use this thing if I need to fear things go wrong, even if I'd be compensated.
Maybe it would provide the right incentives for the companies though.
Though a compensation that high sounds like it would invite fraud, where the customer would be glad to have something go "wrong" and get a fat check. Not sure if that's a solvable problem.