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Kayako vs Pylon: Agentic B2B Support

Kayako and Pylon: Agentic B2B Support both land on Depends.

Kayako

kayako.com

Depends
Confidence: Medium

Buy if you're a mid-size team with real ticket volume that wants AI deflection and seatless pricing.

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Kayako versus Pylon: Agentic B2B Support
CompareKayakoPylon: Agentic B2B Support
VerdictDependsDepends
Best forMid-size support teams (10+ agents)Slack-centric B2B SaaS support teams
Who it's not forTiny teams . a shared inbox or Freshdesk free plan is enoughB2C high-volume ticket teams . Zendesk fits better
PrivacyNo issues found with the current cloud product; legacy self-hosted Kayako Classic carries multiple public CVEs.⁸No known public vulnerabilities found in the sources reviewed.
Support qualityNo direct evidence in sourcesNo direct user evidence found
Public sentimentRatings hover around 4.0-4.1/5: users praise ease of use, while others stay unsure and gripe about pricing.³Independent user reviews are thin in these sources, but cited ratings are strong and Slack-native workflows draw praise.
Biggest gotchaPricing complaints are reviewers' most common theme; confirm true costs before committingStarter enforces a 3-seat minimum; monthly billing raises $59 to $70/seat⁷

Pick Kayako when

  • Mid-size support teams (10+ agents)
  • Ticket-heavy B2B SaaS
  • Teams migrating off Groove or shared inboxes
  • Buyers piloting AI ticket deflection

When Kayako is not a fit

  • Tiny teams . a shared inbox or Freshdesk free plan is enough
  • Anyone needing transparent, predictable pricing before signing
  • Orgs still on self-hosted Kayako Classic without a patch plan
  • Very low ticket volumes where AI automation never pays back

Pick Pylon: Agentic B2B Support when

  • Slack-centric B2B SaaS support teams
  • Teams scaling support with AI agents
  • Migrators off Zendesk wanting AI-native

When Pylon: Agentic B2B Support is not a fit

  • B2C high-volume ticket teams . Zendesk fits better
  • Teams with fewer than 3 agents (seat minimum)
  • Buyers needing published pricing before a sales call
  • Simple email-first shared inbox needs

Sources

  1. Kayako . official sitekayako.com
    official
  2. Kayako Pricingkayako.com
    official
  3. Kayako Reviews 2026 . G2g2.com
    review
  4. Kayako Reviews 2026: Details, Pricing, & Features . G2 pricingg2.com
    review
  5. Kayako Reviews . Trustpilottrustpilot.com
    review
  6. I tested Kayako . TechRadartechradar.com
    review
  7. Kayako Pricing 2026: Is It Worth It? . Featurebasefeaturebase.app
    review
  8. Kayako Fusion v4.51.1891 . multiple web vulnerabilities . Acunetixacunetix.com
    security
  9. CVE-2010-2912 . NVDnvd.nist.gov
    security
  10. June 2016 Security Advisory for Kayako Classicclassichelp.kayako.com
    security
  11. Aurea case study . Kayakokayako.com
    official
  12. Trilogy case study . Kayakogo.kayako.com
    official
  13. DC Advisory: Kayako sale to ESW Capitaldcadvisory.com
    news
  14. Kayako Revenue 2021: $162M ARR . GetLatkagetlatka.com
    news
  15. Pylon: Agentic B2B Support (official)usepylon.com
    official
  16. Pylon on Y Combinatorycombinator.com
    official