For a company utterly dependent on email, Zendesk came across to me as very naive about email sending.

I did a Zendesk integration shortly after working on a general overhaul of our email at a previous company. The overhaul involved separating out our different types (transactional, marketing, support, etc), and then implementing best practices on deliverability for each of them. Not your day-one email setup, but we were still a small company.

The comparison to Zendesk's approach was astounding. Assuming you don't want to use a Zendesk address (we didn't, customers thought it was dodgy), the email setup they let you do was bad, and their support folks had no idea about any of the details. DKIM, SPF, etc, was all alien to them. Ironically they had pretty bad support in general.

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treis 2 hours ago | parent | next [-]

I worked at Zendesk on the email team. I think that's just support being support. The core engineers knew what they were doing.

	▲	otterley 2 hours ago \| parent \| next [-]
		I transitioned Zendesk from their original Exim-based ingress/egress SMTP services to Postfix and set up all the DKIM and SPF stuff long before there was ever a mail team. I worked regularly with large email providers to ensure our egress CIDR blocks were clean. I like to think I knew what I was doing. :-)
	▲	danpalmer 2 hours ago \| parent \| prev [-]
		That's good to know you knew what you were doing! However the product also didn't appear to expose any of the control we needed to have a good email setup. Maybe this is because we weren't paying enough (mentioned in another reply), but we were also never directed to pay more despite asking for this sort of control.

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rpcope1 4 hours ago | parent | prev [-]

> DKIM, SPF, etc, was all alien to them. Ironically they had pretty bad support in general.

So basically good old fashioned "quality" enterprise shitware.

	▲	danpalmer 3 hours ago \| parent [-]
		Not necessarily, our support team kinda loved it. I used the interfaces and it was pretty good software in many ways. They just didn't seem to be very capable when it came to medium complexity email setups. Many of their setup guides literally tell you to log into support address Gmail and set up a forwarding rule to send everything to Zendesk. I suspect the issue is that we weren't paying enough. We had maybe 10 seats. I bet if you're buying 1000 seats a bunch of Zendesk engineers turn up and configure everything for you, but with the robust email setup needing that engineering time on their side to configure... so I guess in that way it may be Enterprise shitware.