WINN.AI, a real-time revenue execution platform that delivers live guidance during customer calls, has raised $18 million in Series A funding. The company said the capital will support continued product development and expansion in the U.S. market.
WINN.AI positions its product as a way for large enterprise sales organizations to translate strategy into consistent, in-the-moment execution. As sales motions become more complex, the company argues that it becomes harder for leaders to ensure every rep adheres to the latest playbooks and best practices during live calls. WINN.AI says its platform provides real-time guidance during conversations while automatically integrating with enterprise CRM and business intelligence systems, aiming to improve win rates, operational efficiency, and playbook adoption.
The company said it has gained traction with large enterprise customers since launching in June 2023, aided by improvements in product efficiency and reasoning capabilities. WINN.AI reported that it tripled annual recurring revenue in 2025, grew 30x over the past two years, and maintained 0% churn among enterprise customers.
WINN.AI also highlighted a set of enterprise examples to illustrate outcomes it attributes to the platform. The company cited Deel as seeing a 33% win rate increase after five months. It said Cyera used WINN.AI to automate capture and improve data consistency, resulting in a doubled CRM fill rate and a 20% increase in playbook usage. WINN.AI also reported that Kaseya synchronized 1,200 reps and reduced administrative time by 98%, attributing the adoption to its integration approach.
To differentiate itself, WINN.AI contrasts proactive, real-time call guidance with what it characterizes as more passive sales AI tools that focus on analyzing recordings after calls are completed.
KEY QUOTES
“Every sales leader knows exactly what a winning call sounds like, but they can’t be in the room to guide it every time. 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.”
“The era of ‘Post-Game Analysis’ is over. 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.”
Eldad Postan-Koren, CEO and Co-Founder, WINN.AI
“WINN.AI allows us to standardize best practices across the entire team by guiding conversations in real-time. That 33% win rate increase proves that consistency drives revenue.”
Olivier Elbaz, Global Head of Expansion, Deel
“You can’t build a data-driven strategy on manual entry -it’s too inconsistent. 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.”
Nate Sintros, Revenue Operations Manager, Cyera
“Scaling a sales team can be challenging, but WINN.AI transforms the process. 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.”
Pablo Dominguez, Operating Partner, Insight Partners
“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. We believe this type of AI co-pilot will empower revenue teams in real-time to sell more effectively and consistently in the future.”
Kevin Jiang, Managing Partner & GP, Mangusta Capital
