Most notably, what we dislike the most so far is that Zendesk couples the Owners account with the Zendesk Admin account. This means that the Owner of the account - the finance person who is actually paying the bill, must have an Administrator/Owner account in Zendesk. That account consumes a license, and the subscription level determines the price of that license. We chose the Enterprise Support with Enterprise Guide so our monthly fee is $155 per user. Being forced to allocate an $1800+/year seat to our finance person, just so we can pay the bill, is frankly ridiculous. Our workaround is to setup the payment information on our Zendesk Administrator's account. That person happens to be in Product Management, halfway around the world from Finance in corporate HQ, and from a finance control, risk management, and administration perspective it raises all sorts of headaches.
There is the additional pain in that Zendesk hides the pricing information behind a login, so the folks that are actually paying the bills cannot log back into the account and easily review pricing if we want to reassess our subscription, unless they have that paid seat. As a workaround to the above-mentioned issue, we added the Finance person to zendesk as a User, for the primary Brand. However, when that person logs in they have no access to the subscription and pricing information, since they do not have Admin privileges. If we try to come back in to the Zendesk pricing page on their website, it leads us through the Get Started flow, forcing us to create an account, etc. Which cannot be done since we already have the account setup.
The whole account Owner concept is poorly executed, and does not seem suitable for Business or Enterprise SaaS software.
As mentioned, we are new to Zendesk, but an additional point of pain has to do with setup for User accounts across Brands. Some subscription levels (which I can't verify since I cannot get to the Subscriptions page), allow you to setup 5 "Brands" or customer portals. Each Brand is a subdomain, e.g. my-portal.zendesk.com. To our best understanding, each Brand portal has a separate login. And you cannot, to our knowledge, use the same login (email) in more than one portal. That's a problem for us. Review collected by and hosted on G2.com.