Do you use any software that you couldn't get help with, or that never could resolve your issues? Did you switch programs, or stick with it despite the poor customer support?
Our experience with Drip this year (2019) has been terrible. We love the software and it's hard to find alternatives that allow us to set up really advanced automations like Drip does, but over the last few months, there have been several bugs that cost us weeks worth of revenue. In those cases, support has been slow and unresponsive—we've had issues open for up to 3 months with no updates from support and no answers to our requests for status updates.
They stop and delete the account for no reason! Then there is no customer service number. But finally managed to get it up back again but still no reasons given!!!
Adobe support is absolutely dismal—unresponsive customer support, dark patterns for canceling (you need to file a support ticket to cancel or adjust licenses downwards), and support options are hidden in a maze of menus. We specifically used it for their Echosign products but switched to Docusign instead.
By such a wide margin (amongst the tools that our team currently uses or has worked with in the past), RingCentral has to take the cake here. Their chat support is slow, the phone support can lead you to believe that they don't really care about customer retention, and the email responses are slow and often incoherent.
Of course, this is all based on our experiences (and it's possible that we've gotten stuck with a few bad apples), but I've been shocked at the general lack of attention placed on the customer experience by the RingCentral team overall. Granted they are a super cheap option for VOIP services but I want to believe they can do better..
By far the worst customer support experience I've had is with eBay, as a seller. Long hold times, and after waiting and getting transferred it's almost impossible to actually get a resolution to your issue. eBay (in many ways understandably) sides with customers by default, offers few ways to help sellers, and if there's a dispute, calling eBay to try to get help won't help. And if you have issues with the software itself, odds are it'll be difficult to resolve as eBay's software is complex and works differently (sometimes with entirely different UI designs) depending on where you click and what you're doing.
eBay's key selling point is that it has a large audience, so you'll sell stuff there faster. But don't expect a great experience in doing so.
Amazon has decent support for customers, but for selling partners (Advantage, Marketplace sellers) it can be absolute hell.
Google Fi is a total disaster if you are outside of the United States. Took me 5 days of countless hours pure agony to buy a phone from them. My order kept getting cancelled.
I've also had really bad experiences with Shipbob.com, Quickbooks, Bank of America, MyUS.com, Shipito, Microsoft . . . so many!
I can't decide which is the worst so I gave this awards to both of them.
Facebook: They banned my Facebook Instant Article without any reason given then I appealed and they said I was not eligible for their monetization program and I swear that I've never broke their rules. But the next day, my Facebook came back to access their monetization program without any reason. Another thing is: You will never talk to 'smart' people in Facebook support. They answer like a robot which made me think am I talking to bot?
Adobe: I was trying to unsubscribe from Adobe's plan and there is no any unsubscribe button. The only way to unsubscribe their product is you need to talk to their support team. So I was try to chat with their support and I have to wait almost 3 hours until someone come to talk to me. Thanks God that I can watch Breaking Bad for two episodes until they come.
My experience w/ Box was only for a Virtual Data Room, so maybe they're just the wrong choice for that use case, but I was floored with how uninformed their sales and support teams were. I needed a click-through NDA, which they twice swore wasn't possible, and it wasn't until I sent them a link from the Box blog about click-through NDAs that they then realized the product they're responsible for selling does in fact have that capability. That has more or less been a microcosm for all the support that followed.