Winn.AI, a Tel Aviv-based startup specializing in artificial intelligence solutions for sales teams, has successfully raised $18 million in a Series A funding round. This significant investment marks a pivotal moment for the company, which aims to revolutionize the way sales representatives engage with prospects through its innovative real-time AI-powered sales assistant. The funding round was co-led by prominent venture capital firms Insight Partners, S Capital, and Mangusta Capital, with additional participation from Moneta VC, HighSage Ventures, Alumni Ventures, Sarona Ventures, and OurCrowd.
Founded in 2022 by Eldad Postan-Koren, who serves as CEO, and Bar Haleva, the CTO, Winn.AI is on a mission to transform traditional sales processes. The company’s flagship product provides sales representatives with an AI assistant that offers real-time guidance during prospect calls. Unlike conventional tools that analyze recorded conversations after they occur, Winn.AI’s technology actively assists sales reps while they are engaged in discussions, ensuring that they ask the right questions and navigate conversations effectively.
The founders of Winn.AI emphasize that their approach is fundamentally different from existing solutions in the market. Eldad Postan-Koren articulated this distinction by stating that most competitors adopt a passive, retrospective stance, focusing on post-mortem analyses of calls to understand why deals were lost. In contrast, Winn.AI takes a proactive approach, providing real-time support that enhances the execution of sales strategies rather than merely analyzing past performance. This shift from analytics to execution is a key selling point for the company, as it addresses a critical pain point for sales teams: the need for immediate feedback and guidance during live interactions.
The funding raised in this Series A round will be instrumental in expanding Winn.AI’s operations, particularly in the United States, which is currently the company’s primary market. The startup has already demonstrated impressive growth, tripling its annual recurring revenue (ARR) in 2025 and achieving a remarkable 30x growth over the past two years. Despite this rapid expansion, Winn.AI is not yet profitable; however, the company is optimistic about its trajectory and plans to use the new capital to bolster its go-to-market team in the U.S. and invest heavily in research and development.
Winn.AI’s customer base includes a diverse range of companies, such as Deel, a leading HR and payroll platform, Kaseya, an IT management solution provider, and Cyera, a data security startup. The company’s revenue model is based on a standard Software as a Service (SaaS) per-seat subscription, making it accessible to organizations of various sizes. As the demand for AI-driven sales solutions continues to grow, Winn.AI is well-positioned to capitalize on this trend.
The startup’s success can be attributed to its ability to adapt to the evolving needs of sales teams. Initially focused on serving account executives, Winn.AI has expanded its target audience to include sales development representatives (SDRs), account managers, solutions engineers, and customer success teams. Interestingly, the company is also witnessing increasing interest from non-sales departments, such as human resources and customer support, indicating the versatility of its AI assistant across different functions within organizations.
The broader landscape of AI and sales technology is thriving, with nearly $4 billion raised in venture capital for companies operating at the intersection of these fields last year. This figure represents a substantial increase compared to previous years, highlighting the growing investor confidence in AI-driven solutions for sales and marketing. While the total amount raised in 2024 was approximately $3.4 billion, it still falls short of the peak funding year of 2021, when startups in this sector raised $6.9 billion.
As Winn.AI continues to gain traction, industry experts are taking notice of its potential to reshape the sales process. Pablo Dominguez, an operating partner at Insight Partners, believes that Winn.AI has the capability to standardize excellence across sales teams, enabling leaders to ensure consistent performance among their representatives. Kevin Jiang, managing partner at Mangusta Capital, describes the company’s offering as an “AI co-pilot” that empowers revenue teams to sell more effectively and consistently in real time.
The implications of Winn.AI’s technology extend beyond mere efficiency gains. By providing real-time insights and guidance, the AI assistant fosters a culture of continuous improvement within sales teams. Representatives can receive immediate feedback on their performance, allowing them to adjust their strategies on the fly and ultimately drive better outcomes. This shift towards real-time coaching is particularly valuable in a fast-paced sales environment, where the ability to adapt quickly can make all the difference in closing deals.
Moreover, the integration of Winn.AI’s solution with existing enterprise customer relationship management (CRM) and business intelligence systems further enhances its value proposition. By streamlining administrative tasks before and after calls, the AI assistant allows sales reps to focus on what they do best: engaging with prospects and building relationships. This holistic approach to sales enables organizations to maximize their resources and improve overall productivity.
As Winn.AI looks to the future, the company is committed to maintaining its momentum and expanding its reach. With plans to enhance its U.S. go-to-market strategy and continue investing in R&D, the startup is poised to solidify its position as a leader in the AI sales assistant space. The growing demand for AI-driven solutions in sales and marketing underscores the importance of innovation in this sector, and Winn.AI is at the forefront of this transformation.
In conclusion, Winn.AI’s recent funding round and its innovative approach to real-time sales assistance highlight the potential for AI to revolutionize the sales process. By providing immediate guidance and support to sales representatives, the company is addressing a critical need in the market and positioning itself for continued growth. As the landscape of AI and sales technology evolves, Winn.AI’s commitment to enhancing the effectiveness of sales teams will undoubtedly play a significant role in shaping the future of how businesses engage with their customers. With a strong foundation and a clear vision, Winn.AI is set to make a lasting impact in the world of sales and marketing.