Just let people cancel imo.
Sometimes all people want is a discount, and as a business losing $20 a month is better than losing a customer.
This is some serious MBA-speak right here. Losing $20 a month is worse than losing a customer. The only time there's a difference is when you're looking to capture enough market in an unsustainable way so that you can paint a good picture for someone dumb enough to acquire you to try to shut down competition.
If you're well-capitalized, then this is just a straightforward monopolization tactic; if you're not well-funded, this is just gaming the numbers so that a well-capitalized monopolist can come in and use you to play the same game.
If you're a company that is trying to be successful and make money, then you're better off using this as a signal about your pricing.
What kind of signal do you have in mind?
It suggests some customers are willing to pay a lower price than other customers. That's not really a surprise, but the numbers are data.
So is the signal that you should lower your price for everyone to something in between, depriving some customers of a service in their happy price range, so that you end up with lower revenue and lose a few more customers as well, but at least you keep a reputation for consistency?
I don't think the GP meant the classic "lose money on each sale but make it up on volume" nonsense, but rather "it is better to forgo $20 of your margin than to lose a customer".
Not to be too much of a jerk about it, but you clearly don't agree. Hard to tell exactly without a end to end demo but it looks like it's at least a couple questions and making sure you click the right button to cancel. And you have to be careful what you click because you swap the "success" button from cancel to accept offer. That's not the same as "just let people cancel".
I'm sure it makes sense from a business perspective. Forcing people to go through a couple questions and click off some offers will increase retention. It's not a big deal. Businesses do lots of things that are annoying to customers because ultimately it makes them more money. Just own that this is what you're doing.