OverloopAI sales prospecting platform that helps teams book more meetings
vs
YeswareSales engagement software that works inside Gmail and Outlook
Comparison · Sales Engagement · weekly run Nov 3
Overloop 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 Overloop.
Choose Overloop if…
- You need CASA Tier 2 or GDPR coverage
Choose Yesware if…
- You want the brand AI engines rank higher (1.8 vs 0)
- You want a free plan to start
- You need SOC 2 Type II coverage
- You prefer a larger, established vendor (51–200 employees)
AI visibility side by side
Latest weekly run · Nov 3
| Metric | Overloop | Yesware |
|---|---|---|
| Visibility score | 0% | 1.8% |
| Change vs last week | down−0.4% | down−0.6% |
| Rank in Sales Engagement | #53 | #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
Overloop −0.4pp · Yesware −0.5999999999999999pp over 1 weekly runs.
Engine by engine
Yesware leads on 3 of 3 engines
ChatGPT
AI Mode
Perplexity
OverloopYesware
Head to head in AI answers
0 engine answers name both brands
0Overloop ranked higher
0Yesware ranked higher
Features, pricing & fit
| Dimension | Overloop | Yesware |
|---|---|---|
| Pricing model | Per seat | Per seat |
| Entry price | $69 per seat / mo | Free; paid from $19 per seat / mo |
| Free plan | No · 7-day trial | Yes |
| Deployment | Cloud | Gmail Chrome extension and Outlook add-in, cloud-hosted on Amazon Web Services and Heroku |
| Compliance | CASA Tier 2, GDPR | SOC 2 Type II |
| Support | Chat support, Email support, Self-onboarding on Starter and Growth, Dedicated Customer Success Manager on Enterprise | Email support, Phone support on Pro and above, Help Center, Weekly webinar trainings |
| Founded | 2015 | 2010 |
| Headquarters | Brussels, Belgium | Saskatoon, SK, Canada |
| Employees | 11–50 | 51–200 |
| Funding | — | Funding round · $48M raised |
| Best for | Sales teams running outbound prospecting that want AI-drafted email and LinkedIn outreach reviewed before it is sent. | 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
Overloop
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, “Overloop vs Yesware”, https://slateindex.ai/compare/overloop-vs-yesware, data of Nov 3, 2026. Licence: CC BY 4.0.