TwentyThe #1 Open Source CRM for modern teams.
vs
YeswareSales engagement software that works inside Gmail and Outlook
Comparison · Sales Engagement · weekly run Nov 3
Twenty vs Yesware
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 for Twenty.
Choose Twenty if…
- You want a lower entry price ($9 vs $19)
Choose Yesware if…
- You want the brand AI engines rank higher (1.8 vs 0)
- You prefer a larger, established vendor (51–200 employees)
- Basic email tracking, templates, and campaigns inside Gmail or Outlook
- Free-forever tier
AI visibility side by side
Latest weekly run · Nov 3
| Metric | Twenty | Yesware |
|---|---|---|
| Visibility score | 0% | 1.8% |
| Change vs last week | no change0% | down−0.6% |
| Rank in Sales Engagement | #58 | #33 |
| Share of voice | 0% | 0.5% |
| Mentions this run | 0 | 4 |
| Positive in AI answers | — | 33% |
The stronger value in each row is marked with a ✓.
Visibility score trend
Weekly runs over the last 60 days
Twenty 0pp · Yesware −0.5999999999999999pp over 1 weekly runs.
Engine by engine
Yesware leads on 3 of 3 engines
ChatGPT
AI Mode
Perplexity
TwentyYesware
Head to head in AI answers
0 engine answers name both brands
0Twenty ranked higher
0Yesware ranked higher
Features, pricing & fit
| Dimension | Twenty | Yesware |
|---|---|---|
| Pricing model | Per seat | Per seat |
| Entry price | Free; paid from $9 per seat / mo | Free; paid from $19 per seat / mo |
| Free plan | Yes | Yes |
| Deployment | Self-hosted or managed cloud | Gmail Chrome extension and Outlook add-in, cloud-hosted on Amazon Web Services and Heroku |
| Compliance | SOC 2 Type II | SOC 2 Type II |
| Support | Community, Email and chat, Priority support, Dedicated support and SLA | Email support, Phone support on Pro and above, Help Center, Weekly webinar trainings |
| Founded | 2023 | 2010 |
| Headquarters | San Francisco, California, United States | Saskatoon, SK, Canada |
| Employees | 1–10 | 51–200 |
| Funding | Series B · $105M raised | Funding round · $48M raised |
| Best for | Technical teams that want a custom CRM they can own, extend with code and adapt as the business grows. | Individual sellers, sales teams and SMBs that sell through email and want simple tools without enterprise overhead |
Plans side by side
Yesware
Free$0seat / month
Pro$19seat / month, billed monthly
Premium$45seat / month, billed monthly
Enterprise$85seat / month, billed monthly
Pros and cons
Themes from the AI answers that mention each brand
Twenty
Profile in progress.
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
Data collected ·ChatGPT, Perplexity, Google AI Mode·coverage 98.8%·next run
Cite as: SlateIndex, “Twenty vs Yesware”, https://slateindex.ai/compare/twenty-vs-yesware, data of Nov 3, 2026. Licence: CC BY 4.0.