Five9 vs Kayako: Which Should You Choose in 2026?
Choosing between Five9 and Kayako comes down to understanding what each tool does best. This comparison breaks down the key differences so you can make an informed decision based on your specific needs, not marketing claims.
Short on time? Here's the quick answer
We've tested both tools. Here's who should pick what:
Five9
Intelligent cloud contact center
Best for you if:
- • You need intelligent cloud contact center
- • You need professional-grade features
Kayako
Unified customer service platform for modern support teams
Best for you if:
- • You want the higher-rated option (7.2/10 vs 0.0/10)
- • Unified customer service platform combining email, chat, and social support
- • Builds complete customer journey maps across all touchpoints
| At a Glance |  Kayako | |
|---|---|---|
Price | Paid | Paid |
Best For | AI for Customer Service | AI for Customer Service |
Rating | —/100 | 72/100 |
| Feature | Five9 | Kayako |
|---|---|---|
| Pricing Model | Paid | Paid |
| Editorial Score | — | 72 |
| Community Rating | No ratings yet | No ratings yet |
| Total Reviews | 0 | 0 |
| Community Upvotes | 161 | 0 |
| Categories | AI for Customer ServiceWorkflow Automation | AI for Customer ServiceWorkflow Automation |
Understanding the Differences
Both Five9 and Kayako solve similar problems, but they approach them differently.Five9 positions itself as "intelligent cloud contact center" while Kayakofocuses on "unified customer service platform for modern support teams". These differences matter depending on what you're trying to accomplish.
When to Choose Five9
Five9 makes sense if you're looking for a comprehensive paid solution.
When to Choose Kayako
Kayako is worth considering if you need a professional-grade tool. Scoring 72/100, it edges ahead in our evaluation.
Who Should Use What?
Bootstrapped or small team?
Neither is free, but both have their value. Test them both and see which clicks.
We'd pick: Kayako
Growing fast?
Your team doubled last quarter and you need tools that won't break when you add 50 more people. Kayako is built for teams that are leveling up.
We'd pick: Kayako
Enterprise with complex needs?
You need SSO, compliance certifications, and a support team that picks up the phone. Five9 is built for organizations like yours.
We'd pick: Five9
Still not sure? Answer these 3 questions
How much can you spend?
Both are paid tools. If money isn't the issue, go with Kayako—it scored higher.
Do you care what other users think?
Both have similar review counts. Read a few before you commit.
Expert opinion or crowd wisdom?
Our team rated Kayako higher (72/100). But the community has upvoted Five9 more (161 votes). Pick your source of truth.
Key Takeaways
What Kayako Does Better
- Higher overall score (72/100)
- Our recommendation for most use cases
Consider Five9 If
- Its specific features better match your workflow
- You prefer its interface or design approach
The Bottom Line
If we had to pick one, we'd go with Kayako (72/100). But the honest answer is that "better" depends on your situation. Kayako scores higher in our analysis, but Five9 might be the right choice if its specific strengths align with what you need most. Take advantage of free trials to test both before committing.
Frequently Asked Questions
Is Five9 or Kayako better?
Based on our analysis, Kayako scores higher with 72/100. Five9 ispaid while Kayako is paid. The best choice depends on your specific needs and budget. We recommend testing both with free trials if available.
Can I switch from Five9 to Kayako easily?
Migration difficulty varies. Check if both tools support data export/import in compatible formats. Some tools offer migration assistance or have integration partners who can help with the transition.
Do Five9 and Kayako offer free trials?
Most software in this category offers free trials or free tiers. Five9 is paid with potential trial.Kayako is paid with potential trial. Visit their websites for current trial offers.