OutplayThe all-in-one sales stack for new-age teams.
vs
YeswareSales engagement software that works inside Gmail and Outlook
Comparison · Sales Engagement · weekly run Nov 3
Outplay 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 0.7 for Outplay.
Choose Outplay if…
- transparent pricing
Choose Yesware if…
- You want the brand AI engines rank higher (1.8 vs 0.7)
- You want a lower entry price ($19 vs $39)
- AI answers describe it more positively (33% vs 0% positive)
- Basic email tracking, templates, and campaigns inside Gmail or Outlook
AI visibility side by side
Latest weekly run · Nov 3
| Metric | Outplay | Yesware |
|---|---|---|
| Visibility score | 0.7% | 1.8% |
| Change vs last week | up+0.7% | down−0.6% |
| Rank in Sales Engagement | #39 | #33 |
| Share of voice | 0.1% | 0.5% |
| Mentions this run | 1 | 4 |
| Positive in AI answers | 0% | 33% |
The stronger value in each row is marked with a ✓.
Visibility score trend
Weekly runs over the last 60 days
Outplay +0.7pp · Yesware −0.5999999999999999pp over 1 weekly runs.
Engine by engine
Yesware leads on 2 of 3 engines
ChatGPT
AI Mode
Perplexity
OutplayYesware
Head to head in AI answers
0 engine answers name both brands
0Outplay ranked higher
0Yesware ranked higher
Features, pricing & fit
| Dimension | Outplay | Yesware |
|---|---|---|
| Pricing model | Per seat | Per seat |
| Entry price | Free; paid from $39 per seat / mo | Free; paid from $19 per seat / mo |
| Free plan | Yes | Yes |
| Deployment | — | 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 | Chat support, Dedicated success manager (Enterprise plan) | Email support, Phone support on Pro and above, Help Center, Weekly webinar trainings |
| Founded | 2019 | 2010 |
| Headquarters | Wilmington, Delaware, US | Saskatoon, SK, Canada |
| Employees | 51–200 | 51–200 |
| Funding | Majority stake acquired by JungleWorks · $9M raised | Funding round · $48M raised |
| Best for | Sales teams of all sizes, especially growing SMBs that want enterprise-level sales engagement at a lower price. | Individual sellers, sales teams and SMBs that sell through email and want simple tools without enterprise overhead |
Plans side by side
Outplay
Free Forever$0free forever
Starter$39month, billed annually
Growth$89user per month, billed annually
Enterprise$139user per month, billed annually
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
Outplay
- transparent pricing
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, “Outplay vs Yesware”, https://slateindex.ai/compare/outplay-vs-yesware, data of Nov 3, 2026. Licence: CC BY 4.0.