WINN.AI, the real-time revenue execution platform delivering live guidance during customer calls, announced it has raised $18 million in Series A funding. The round was led by global software investor Insight Partners, Mangusta Capital and S Capital, with participation from Moneta, Highsage, Alumni Ventures, Sarona Ventures, and OurCrowd.
The funding comes as WINN.AI found traction with large enterprise customers since launching in June 2023. Over the past year, improvements to the efficiency and reasoning ability of WINN.AI’s product positioned the company to accelerate growth. As a result, WINN.AI tripled annual recurring revenue (ARR) in 2025 alone while growing by 30X over the past two years and maintaining a 0% churn rate among enterprise customers.
WINN.AI’s live assistant addresses the challenge of maintaining sales consistency across large enterprise teams. As sales processes become more complex, organizations can struggle to ensure reps apply the latest playbooks and best practices during customer conversations. WINN.AI’s platform delivers real-time guidance during live calls while automatically integrating with enterprise CRM and business intelligence systems, a combination that has driven measurable improvements in win rates, operational efficiency, and playbook adoption across its customer base.
“Every sales leader knows exactly what a winning call sounds like, but they can’t be in the room to guide it every time,” said Eldad Postan-Koren, CEO and Co-Founder of WINN.AI. “We let AI handle the ‘science’ of the sale so the rep is free to master the ‘art’ of the connection. Our customers see the quality of conversations rise immediately: the AI ensures consistency, and the human ensures trust.”
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Real Impact: Three Enterprise Case Studies
WINN.AI’s delivered measurable results across different use cases:
- Win Rate Improvement (Deel): The global HR-tech company saw win rates jump 33% after five months with WINN.AI. “WINN.AI allows us to standardize best practices across the entire team by guiding conversations in real-time,” said Olivier Elbaz, Global Head of Expansion at Deel. “That 33% win rate increase proves that consistency drives revenue.”
- Structured Data & Adherence (Cyera): The data security unicorn turned to WINN.AI to eliminate data gaps and standardize execution. “You can’t build a data-driven strategy on manual entry -it’s too inconsistent,” said Nate Sintros, Revenue Operations Manager at Cyera. “WINN.AI automated the capture. Our CRM fill rate doubled and playbook usage jumped 20%, turning our biggest blind spot into our most reliable data asset.”
- Efficiency at Scale (Kaseya): The IT management powerhouse synchronized 1,200 reps and slashed admin time by 98%. WINN.AI’s seamless integration enabled instant adoption, allowing the organization to modernize execution at scale without the friction.
What Makes WINN.AI Different
“The era of ‘Post-Game Analysis’ is over,” said Eldad Postan-Koren, CEO of WINN.AI. “Traditional Sales AI is passive – recording calls to tell you why you lost. WINN.AI is proactive. We don’t analyze the past; we shape the present. By guiding execution in real-time, we change the outcome while the customer is still on the call.”
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The Series A will fund U.S. market expansion and continued product development.
“Scaling a sales team can be challenging, but WINN.AI transforms the process” said Pablo Dominguez, Operating Partner at Insight Partners. “It helps leaders to standardize excellence across every rep, delivering higher playbook adoption. For a sales leader, this shift can bring teams closer to delivering consistency.”
“We invested in WINN.AI because we see its real-time AI assistant fundamentally reshaping how sales gets done – automating busywork, improving CRM data quality, and guiding reps live on calls to boost execution and close rates,” said Kevin Jiang, Managing Partner & GP at Mangusta Capital. “We believe this type of AI co-pilot will empower revenue teams in real-time to sell more effectively and consistently in the future.”
