WINN. AI, a startup that offers real-time guidance to sales teams during customer calls, announced on Wednesday that it has secured $18 million in Series A funding. The funding round was led by Insight Partners, Mangusta Capital, and S Capital, with additional investments from Moneta, Highsage, Alumni Ventures, Sarona Ventures, and OurCrowd. This latest investment comes amid growing traction with large enterprise clients since the company’s launch in June 2023. WINN. AI attributed its accelerated growth over the past year to enhancements in the efficiency and reasoning capabilities of its platform. The company reported tripling its annual recurring revenue in 2025 and achieving a 30-fold growth over the past two years, all while maintaining a 0% churn rate among enterprise customers. WINN. AI’s platform is specifically designed to tackle the challenge of ensuring consistent sales execution across large teams. As sales processes grow more complex, companies often find it difficult to guarantee that representatives follow the latest playbooks and best practices during live conversations. The platform offers real-time prompts and guidance during calls and integrates seamlessly with enterprise CRM systems and business intelligence tools. Customers have noted measurable improvements in win rates, operational efficiency, and playbook adoption through its use. “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, WINN. AI’s co-founder and CEO. “We let AI manage the 'science' of the sale so the rep can focus on mastering the 'art' of connection. ” Among the company’s cited clients, Deel, a global HR technology firm, reported a 33% increase in win rates after five months of using WINN. AI, according to Olivier Elbaz, their global head of expansion. Cyera, a data security company, noted it doubled its CRM data fill rate and increased playbook usage by 20% following adoption of the platform, shared Nate Sintros, its revenue operations manager. Kaseya, an IT management firm, stated the system helped coordinate 1, 200 sales reps and cut administrative time by 98%.

Postan-Koren emphasized that WINN. AI distinguishes itself from traditional sales analytics solutions by focusing on live execution rather than analyzing calls after the fact. “The era of 'Post-Game Analysis' is over, ” he said. “Traditional Sales AI is passive — recording calls to explain why you lost. WINN. AI is active. We don’t analyze the past; we shape the present. By guiding execution in real-time, we change outcomes while the customer is still on the call. ” WINN. AI plans to use the Series A proceeds to expand further into the U. S. market and advance product development. Pablo Dominguez, an operating partner at Insight Partners, noted the platform aids sales leaders in standardizing execution across teams and boosting adherence to sales playbooks. Kevin Jiang, managing partner at Mangusta Capital, explained the firm invested in WINN. AI due to its belief that real-time AI assistants will revolutionize sales by automating administrative tasks, enhancing CRM data quality, and supporting representatives during live calls.