Winn.ai, which has built an artificial intelligence-powered sales assistant, has raised $18 million in a Series A funding round, the company tells Crunchbase News exclusively.
The company provides sales reps with a real-time AI assistant that “guides” them during a prospect call while integrating with enterprise CRM and business intelligence systems. It also aims to eliminate administrative tasks before and after the call.
The Tel Aviv-based startup was co-founded by CEO Eldad Postan-Koren and CTO Bar Haleva.
The biggest difference between Winn and other startups in the space is timing, according to Postan-Koren.
“Most players in the market are passive and retrospective — they record calls to analyze after the fact why a deal was lost — a ‘post-mortem’ approach,” he told Crunchbase News. “Winn is proactive and real-time. We don’t just analyze history — we help the rep navigate the conversation while it’s happening to ensure the right questions are asked.”
The focus, compared to other conversation intelligence tools, is execution vs. analytics, according to Winn’s co-founders.
“Coaching is hard to apply when the feedback comes a week later,” Postan-Koren said. “Instead of telling a rep what they should have done, we guide them on what to do right now.”
Insight Partners, S Capital and Mangusta Capital co-led the Series A raise, which included participation from Moneta VC, HighSage Ventures, Alumni Ventures, Sarona Ventures and OurCrowd. In total, the startup has raised $35 million since its 2022 inception.
Companies at the intersection of AI and sales and marketing raised close to $4 billion in venture capital last year, per Crunchbase data. That represents a sizable increase over the $3.4 billion raised by such startups in 2024, though remains lower than the $6.9 billion raised in the peak venture funding year of 2021 or the $5 billion raised in 2022.
Growth and expansion
Postan-Koren declined to provide hard financial figures for Winn, saying only that it tripled its annual recurring revenue in 2025 and that it has achieved 30x growth over the past two years.
Winn has dozens of customers, including HR and payroll company Deel, IT management platform Kaseya, and data security startup Cyera. The company’s revenue model is a standard SaaS per-seat subscription.
The company is not yet profitable. It plans to use its new capital to expand its U.S. go-to-market team, while continuing to invest “heavily” in R&D. Presently, Winn has over 40 employees.
Its primary market is the U.S., although Postan-Koren said it is seeing “strong organic traction” in the United Kingdom and Europe. It is also expanding its target user, he said.
“We started with a laser focus on account executives,” Postan-Koren explained. “However, the demand quickly pulled us into other departments.”
The company now also works with sales development representatives, account managers, solutions engineers and customer success. Interestingly, he said that Winn is also starting to see demand from nonsales teams, such as support and HR.
Pablo Dominguez, operating partner at Insight Partners, believes that Winn “transforms the process” of scaling a sales team.
“It helps leaders to standardize excellence across every rep, delivering higher playbook adoption,” he said in a statement. “For a sales leader, this shift can bring teams closer to delivering consistency.”
Kevin Jiang, managing partner and general partner at Mangusta Capital, described Winn’s offering as an AI co-pilot that can “empower revenue teams in real time to sell more effectively and consistently in the future.”
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Illustration: Dom Guzman
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