Just migrated a team of 20 off Kayako after a decade. Everyone's cheering about Zendesk's "modern" UI. Meanwhile, the actual work got harder.
What we "gained":
* Another monthly SaaS bill that doubled for the same agent count.
* A reporting module that requires a PhD to filter by something simple like "tickets opened by source last quarter."
* Endless marketplace apps to replicate basic Kayako functions. More points of failure.
What we lost:
* **Sensible automation.** Kayako's rules were straightforward. Now we're building "triggers" with this nonsense:
```json
{
"conditions": {
"all": [
{"field": "status", "operator": "less_than", "value": "closed"}
]
}
}
```
It's JSON for a status check. Why.
* **Actual control over ticket queues.** Their "views" are sluggish and forget custom sorting.
* **A sane audit log.** Good luck tracing who changed what and when.
The integration hype is real, but the core help desk job—route, resolve, report—is now buried under layers of "features." The support platform market is solving problems we didn't have.
-- old school
-- old school
I'm a junior ops manager at a 40-person B2B SaaS shop. We handle about 800 tickets a month and I was thrown into evaluating our help desk last year after we outgrew email. I've had Zendesk in production for about 18 months and did a deep trial of Kayako before we signed.
My side-by-side for what you're describing:
1. **Automation Simplicity vs. Power:** Kayako's rule builder is way more intuitive for quick "if-this-then-that" logic. Zendesk's triggers and automations are far more granular, but you hit the complexity wall fast. For your JSON example, the trade-off is that Zendesk's system can hook into many more custom ticket fields and external conditions, but you need a dedicated admin to build and maintain them properly.
2. **Real Total Cost:** Our bill for 20 agents on Zendesk Support (Professional) is about $1,600/month. Kayako's equivalent unlimited plan was roughly half that when we quoted. The hidden cost is the marketplace: budget an extra $30-50/agent/month for essential apps to get basic functionality like queue management or SLA timers that Kayako includes.
3. **Queue and View Management:** You're right about custom sorting. Zendesk views are powerful filters, but they're static lists. Any custom sort you manually apply isn't saved. Kayako's persistent, sortable queues were better for managing a high-volume, specialized workflow. Zendesk expects you to use custom views and tags for everything, which adds clicks.
4. **Reporting and Audit:** Zendesk Explore is a full business intelligence tool, overkill for most support teams. Building a simple report takes 10-15 clicks. Kayako's built-in reports were basic but accessible. For audit logs, Zendesk logs the "what" but often obscures the "who" in system entries unless you pay for their higher-tier add-ons.
I'd recommend sticking with Kayako if your core need is a straightforward, agent-centric ticketing system that your whole team can configure without training. If you're forced onto Zendesk because of executive demand for its brand name or deep ecosystem (like required integrations with Salesforce or Jira), then you need two things: a dedicated system admin and a budget for at least three critical marketplace apps. What are your non-negotiable integrations, and how much time can you spare for weekly system tinkering?