With "legacy industries" in particular, their websites are usually so busted with short session timeouts/etc that it's worth spending a few minutes on hold to get somebody else to do it.

We've found that just a "Hey, how can I help?" will get many of these customers to dump every problem they've ever had on you, and if you can make turn two actually productive, then the odds of someone dropping out of the interaction is low.

The difference between "I need to cancel my subscription!" leading to "I can help with that! To find your subscription, what's your phone number?" or "The XYZ subscription you started last year?" is huge.