Crosby vs Winn.ai
Crosby vs Winn.ai, compared side by side on 19 data points: what each one does, how big it is, what it has raised, the tech running each site, and what users report. We score both out of 100 on traction, team and visibility: Crosby is on 58/100 and Winn.ai on 54/100.
Where each one leads
Crosby
- our overall score: 58/100 against 54/100
- funding raised: $85.8M against $17.0M
Winn.ai
- headcount: 75 against 20
At a glance
| Measure | Crosby | Winn.ai |
|---|---|---|
| What it is | An AI-powered law firm that reviews and negotiates contracts at high speed for startups. | Real-time AI assistant for sales teams to improve deal closing and CRM management. |
| Category | Sales, CRM, AI Legal, LegalTech | Enterprise, Sales, CRM, Intelligence |
| Sells toBusiness model | B2B | B2B |
| Offering | Services | Software |
| Founded | 2024 | 2021 |
| Headquarters | San Francisco, United States | Tel Aviv, Israel |
| Status | Active | Active |
Size, funding and growth
| Measure | Crosby | Winn.ai |
|---|---|---|
| Employees | 20 | 75 |
| Headcount growthLast 12 months | Not published | +33.0% |
| Total funding | $85.8M | $17.0M |
| Latest round | Series B | Seed |
| LinkedIn followers | Not published | 21,803 |
StartupHub scores
Our own 0-100 ratings. They measure company strength and site quality, not which product suits you.
| Measure | Crosby | Winn.ai |
|---|---|---|
| StartupHub scoreOur 0-100 rating | 58/100 | 54/100 |
| Traction | 53/100 | 55/100 |
| Team | 60/100 | 50/100 |
| Community | 8/100 | Not published |
| Search visibility | 19/100 | 26/100 |
| Quality | 68/100 | 58/100 |
| Agent readinessHow well an AI agent can read and act on the site | D (46/100) | D (50/100) |
| Domain ratingLink authority, 0-100 | 45/100 | 47/100 |
Technology
Detected on each public site, so it reflects the marketing stack as well as the product.
| Measure | Crosby | Winn.ai |
|---|---|---|
| Hosting | AWS | Not detected |
| CDN | CloudFront | Cloudflare |
| CMS | Not detected | WordPress |
| Frameworks | Not detected | Jquery, Bootstrap |
| Analytics | Google Tag Manager, PostHog | Segment |
| Support stack | Not detected | HubSpot |
Crosby vs Winn.ai: common questions
Which is better, Crosby or Winn.ai?
On our 0-100 score Crosby rates higher (58/100 against 54/100). The score weights traction, team, visibility and profile completeness, so it reflects company strength rather than which product suits you. We compare the two on 19 data points above: read the rows that match what you are buying for.
How do Crosby and Winn.ai compare on the numbers?
Crosby leads on our overall score (58/100 against 54/100), funding raised ($85.8M against $17.0M). Winn.ai leads on headcount (75 against 20).
Read the full Crosby review and pricing or the Winn.ai review and pricing. You can also browse other Crosby alternatives we track.

