YeswareSales engagement software that works inside Gmail and Outlook
vs
ZendeskAI-powered customer service platform
Comparison · Sales Engagement · weekly run Nov 3
Yesware vs Zendesk
Which one do AI engines recommend, and how do they differ on price, fit and features?
The short answer
Yesware is the stronger AI pick in Sales Engagement: it has a visibility score of 1.8 versus 0.4 for Zendesk.
Choose Yesware if…
- You want the brand AI engines rank higher (1.8 vs 0.4)
- You want a free plan to start
- Basic email tracking, templates, and campaigns inside Gmail or Outlook
- Free-forever tier
Choose Zendesk if…
- AI answers describe it more positively (34% vs 33% positive)
- You need ISO 27001:2022 or ISO 27018:2019 or ISO 27701:2019 or ISO 27017:2015 or ISO 42001:2023 or FedRAMP LI-SaaS or Cyber Essentials Plus coverage
- You prefer a larger, established vendor (5,000+ employees)
- Industry leader in omnichannel customer support
AI visibility side by side
Latest weekly run · Nov 3
| Metric | Yesware | Zendesk |
|---|---|---|
| Visibility score | 1.8% | 0.4% |
| Change vs last week | down−0.6% | up+0.1% |
| Rank in Sales Engagement | #33 | #40 |
| Share of voice | 0.5% | 0.1% |
| Mentions this run | 4 | 1 |
| Positive in AI answers | 33% | 34% |
The stronger value in each row is marked with a ✓.
Visibility score trend
Weekly runs over the last 60 days
Yesware −0.5999999999999999pp · Zendesk +0.10000000000000003pp over 1 weekly runs.
Engine by engine
Yesware leads on 1 of 3 engines
ChatGPT
AI Mode
Perplexity
YeswareZendesk
Head to head in AI answers
0 engine answers name both brands
0Yesware ranked higher
0Zendesk ranked higher
Features, pricing & fit
| Dimension | Yesware | Zendesk |
|---|---|---|
| Pricing model | Per seat | Per seat |
| Entry price | Free; paid from $19 per seat / mo | $19 per seat / mo |
| Free plan | Yes | No |
| Deployment | Gmail Chrome extension and Outlook add-in, cloud-hosted on Amazon Web Services and Heroku | Cloud (SaaS) |
| Integrations | — | 1800+ |
| Compliance | SOC 2 Type II | SOC 2 Type II, ISO 27001:2022, ISO 27018:2019, ISO 27701:2019, ISO 27017:2015, ISO 42001:2023, FedRAMP LI-SaaS, Cyber Essentials Plus |
| Support | Email support, Phone support on Pro and above, Help Center, Weekly webinar trainings | Help Center, Community, Partners |
| Founded | 2010 | 2007 |
| Headquarters | Saskatoon, SK, Canada | San Francisco, California, United States |
| Employees | 51–200 | 5,000+ |
| Funding | Funding round · $48M raised | Take-private (Hellman & Friedman, Permira) |
| Best for | Individual sellers, sales teams and SMBs that sell through email and want simple tools without enterprise overhead | Support teams from startups to enterprises that need omnichannel ticketing with AI automation |
Plans side by side
Yesware
Free$0seat / month
Pro$19seat / month, billed monthly
Premium$45seat / month, billed monthly
Enterprise$85seat / month, billed monthly
Zendesk
Support Team$19agent/month paid yearly
Suite Team$55agent/month paid yearly
Suite Professional$115agent/month paid yearly
Suite Enterprise + CopilotCustomcontact sales
Pros and cons
Themes from the AI answers that mention each brand
Yesware
- Basic email tracking, templates, and campaigns inside Gmail or Outlook
- Free-forever tier
- Offers a free tier
- Suited to individual reps or very small teams
- Likely cheaper for solo operators
Zendesk
- Industry leader in omnichannel customer support
- Scalable platform for large enterprise teams
- Mature ticketing operations and SLA management
- Extensive marketplace and broad integrations
- Free trial available for 14 days
- Heavy, slow deployment compared with lighter tools
- High per-agent costs
- AI add-ons billed separately on top of base fee
Data collected ·ChatGPT, Perplexity, Google AI Mode·coverage 98.8%·next run
Cite as: SlateIndex, “Yesware vs Zendesk”, https://slateindex.ai/compare/yesware-vs-zendesk, data of Nov 3, 2026. Licence: CC BY 4.0.