Earlier quoted context omitted.
I hope he doesn't. It sounds like your customer service is the usual cost-minimization nightmare, and I don't see how fixing this one case will make it any better. Companies like yours make it hard for customers to reach capable representatives and routinely break service promises. Because hey! who cares if we have treated people decently? it has nothing to do with the business model. There must be dozens of ways to…
You should notice that a CEO may not necessarily be aware of everything going on, and cases like this might trigger a deeper look on his side. Whether affirm has this kind of issues as a pattern or not, i don't know. But assuming malintent is not a great pov imho.
"Everything" in the micro sense, sure. "Everything" in the macro sense, well, that's literally the job description of CEO, so it sounds like you think the CEO does not deserve criticism. If customer service is not working to the benefit of customers, I'd say that's something a CEO should already be aware of and represents a lack in organizational awareness, which compromises executive duties.
Just because the job is hard doesn't mean we should give anyone a break. Assuming the role and responsibilities of CEO is completely voluntary.
I don't think anyone is assuming malice; intent has nothing to do with this. The outcome of each interaction is only what matters here.