Key Takeaways
- WINN.AI, a Tel Aviv-based startup founded in 2022, raised $18 million in Series A funding led by Insight Partners, Mangusta Capital, and S Capital, bringing total funding to $35 million.
- The platform delivers live AI guidance during sales calls, automates CRM updates, and integrates with systems like Salesforce and HubSpot for enterprise teams.
- Customers including Deel (33% win rate increase), Cyera (doubled CRM fill rate), and Kaseya (98% admin time reduction) validate impact; ARR tripled in 2025 with 30x growth over two years.
- Funds will fuel U.S. expansion, R&D, and team growth beyond 40 employees.
Quick Recap
Tel Aviv-based WINN.AI announced an $18 million Series A funding round on February 10, 2026, to advance its real-time revenue execution platform that provides AI-driven guidance during live customer calls.
Led by Insight Partners with Mangusta Capital, S Capital, and others including OurCrowd, the investment brings total capital to $35 million since the 2022 founding by CEO Eldad Postan-Koren and CTO Bar Haleva. The official announcement came via Business Wire and Insight Partners’ channels.
.@Winn_sales raises $18 million Series A to bring real-time AI guidance to sales teams.
— CTech (@Calcalistech) February 11, 2026
The Israeli startup’s platform listens, guides, and provides answers in real time, helping reps focus on human connection.https://t.co/L6fMsxJjm4
Platform Details and Funding Breakdown
WINN.AI’s core technology acts as a proactive AI co-pilot, offering real-time prompts to ensure playbook adherence (e.g., MEDDIC, SPICED, BANT), capturing call insights, and syncing data seamlessly with Salesforce, HubSpot, and BI systems – slashing manual entry by up to 98% in case studies.
The $18M will primarily fund U.S. market penetration, where WINN.AI already serves dozens of customers like Deel, Cyera, and Kaseya, and heavy R&D to broaden use cases beyond sales to customer success and HR. Investors praised its execution focus: Insight’s Pablo Dominguez noted it “standardizes excellence” for scaling teams, while Mangusta’s Kevin Jiang called it an “AI co-pilot for consistent selling.”
Real-Time Guidance and Automated CRM Capture
Unlike tools that mainly review calls after they end, Winn.AI is designed to listen during the call, detect objections or technical questions, and surface exact answers from the company’s internal knowledge base. The same workflow is intended to reduce note-taking and improve CRM hygiene through direct integrations with CRM and BI systems.
The funding narrative is strongly tied to measurable execution outcomes. In the company’s published case studies, Deel reported a 33% win-rate jump after five months; Cyera cited a 2x improvement in CRM fill rate and a 20% increase in playbook usage; and Kaseya highlighted scale impact across 1,200 reps with a 98% cut in admin time.
On product ROI, Winn.AI’s own website also markets quantified performance claims such as 30% higher playbook adoption (in 4 weeks), 9x higher CRM fill rate, and 85% less admin work, which indicates the company is positioning itself as a revenue execution layer, not only a transcription tool.
Why This Matters Now?
Sales AI has been crowded for years, but most tools have leaned on retrospective call recording and analysis. Winn.AI is explicitly betting that “in the moment” guidance changes outcomes while the buyer is still on the call, which reduces the delay between coaching and behavior change.
Market timing also supports this: venture funding into startups at the intersection of AI and sales and marketing was reported at nearly $4B last year, showing sustained investor appetite for workflow-native AI that ties directly to revenue execution.
Competitive Landscape
| Feature/Metric | WINN.AI | AIROI | Saliently |
| Funding Raised | $35M | Undisclosed seed | Undisclosed |
| Pricing (per user/mo) | $59-$69 | Undisclosed | $25+ (Starter est.) |
| Latency (feedback) | Real-time (<5s est.) | Real-time | <3.5s |
| Customers/Growth | 30x ARR, zero churn | Emerging | Emerging |
| Context Window | CRM-integrated scale | Multi-turn memory | Screen + audio |
| Multimodal Support | Audio/CRM/BI | Audio/screen | Audio/transcript |
| Agentic Capabilities | Playbook prompts/auto-CRM | Deal suggestions | BANT nudges |
Bayelsa Watch’s Takeaway
In my experience analyzing fintech and enterprise SaaS funding waves, WINN.AI’s $18M raise is a big deal because it validates real-time AI as the next frontier for sales efficiency, especially with proven metrics like 33% win rate lifts at clients like Deel.
I think this is bullish for adoption in B2B tech stacks – proactive coaching crushes passive analytics, and with U.S. expansion, expect Winn to challenge incumbents while boosting user quotas in a crowded RevOps market. As someone tracking insurtech parallels, its CRM automation could redefine risk-managed sales plays too.
