Outreach vs Winn.AI
Which Sales AI tool is better in 2026?
Outreach
AI sales execution platform for outbound at enterprise scale.
Winn.AI
Real-time AI revenue execution that guides reps and automates CRM work on calls
Side-by-side
Outreach leads on both fronts — more capital raised ($489M) and a lower entry price than Winn.AI.
| Metric | Outreach | Winn.AI |
|---|---|---|
| Taglinei | AI sales execution platform for outbound at enterprise scale. | Real-time AI revenue execution that guides reps and automates CRM work on calls |
| Foundedi | 2014🏆 | 2022 |
| HQi | Seattle, US | Tel Aviv, IL |
| Employeesi | 501-1000🏆 | 11-50 |
| Neuron scorei | 64🏆 | 57 |
| Total fundingi | $489M🏆 | $31M |
| Latest roundi | Series G · Jun 2021 | Series A · Feb 2026 |
| Valuationi | $4.4B🏆 | — |
| Cheapest paid plani | From $100/mo🏆 | Pricing not disclosed |
| Free plani | ✗ | ✗ |
| Free triali | ✗ | ✓ |
| Top tier pricei | Pricing not disclosed | Pricing not disclosed |
| Pricing summaryi | Enterprise · From $100/mo | Free trial |
| Categoriesi |
Capability matrix
Developer-facing capabilities and access signals for Outreach and Winn.AI.
| Capability | Outreach | Winn.AI |
|---|---|---|
| MCP support | ✗ | ✗ |
| Public API | ✗ | ✓ |
| Webhooks | ✗ | ✗ |
| OAuth 2.0 | ✗ | ✗ |
| SDK languages | 2 (JavaScript, Python) | — |
| Free plan | ✗ | ✗ |
| Free trial | ✗ | ✓ |
| Verified | ✗ | ✗ |
| Active deal | ✗ | ✗ |
🟢 Strengths of Outreach
- Has raised more capital ($489M vs $31M)
- Higher Neuron score (64 vs 57)
- Lower starting price ($100/mo)
- More mature (2014)
🔵 Strengths of Winn.AI
- Offers a free trial
- Newer company (2022)
Which should you choose?
Choose Outreach if price matters most — it starts at Enterprise · From $100/mo, which is friendlier for teams watching burn. Both AI Sales tools ship core features, so the cost delta often decides it for small teams and solo operators.
Choose Outreach if you want the most established option — it has raised $489M, suggesting more runway for enterprise features, support, and long-term roadmap. For mission-critical workflows or larger teams, that stability often outweighs a lower monthly price.
Frequently asked questions
Outreach vs Winn.AI — which is better?
It depends on your priority. Outreach has raised more capital and is the more established option; Winn.AI has broader feature depth. See the side-by-side table above.
Is Outreach cheaper than Winn.AI?
Yes — Outreach's cheapest paid plan is Enterprise · From $100/mo, while Winn.AI's is Free trial.
Do Outreach and Winn.AI offer free plans?
Outreach: Paid only. Winn.AI: Free trial only.
Explore more AI Sales tools
Contextual paths to related AI startups, deals and rankings.