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Winn.ai raises $18M Series A to bring real-time AI guidance to sales teams

AI sales platform Winn.ai secures $18M Series A to deliver live guidance and automate CRM updates.

Celi Anindia

12 Feb 2026 • 3 min read

Winn.ai, a Tel Aviv-based startup, has secured $18 million in Series A funding to expand its real-time AI sales assistant platform. The round was led by Insight Partners, Mangusta Capital, and S Capital, with participation from several other investors. Winn.ai’s platform is designed to help large enterprise sales teams bridge the gap between sales strategy and execution by providing live guidance during customer calls and automating CRM data capture.

Short on time?

Here’s a quick look at what’s inside:

Who is Winn.ai, and why does this funding matter?

Founded in 2022 by Eldad Postan-Koren and Bar Haleva, Winn.ai has quickly gained traction with enterprise customers in the US and Europe. The company’s platform focuses on real-time sales execution, offering live coaching and guidance during customer calls. Since its launch, Winn.ai has tripled its annual recurring revenue and maintained a 0% churn rate among enterprise clients, including Deel, Cyera, and Kaseya.

The $18 million Series A round brings Winn.ai’s total funding to $35 million. The new capital will support US market expansion and further product development, as the company aims to help more organizations standardize sales excellence and improve operational efficiency.

How Winn.ai’s real-time assistant works for marketers

Winn.ai’s platform is built to address a common challenge: ensuring sales teams consistently apply best practices during live customer conversations. Here’s how it works in practice:

Live call guidance: The AI assistant provides real-time prompts and coaching during sales calls, helping reps follow playbooks and ask the right questions.
Automated CRM updates: Key information from calls is automatically captured and synced with enterprise CRM and business intelligence systems, reducing manual data entry and improving data quality.
Playbook adherence: The platform helps standardize execution across large teams, making it easier to roll out new strategies and ensure consistent messaging.
Efficiency gains: By automating administrative tasks, Winn.ai frees up sales reps to focus on building relationships and closing deals.

For marketers, this means better alignment between sales and marketing strategies, more reliable data for campaign analysis, and improved win rates across the sales funnel.

What sets Winn.ai apart in the sales tech landscape

The sales tech market is crowded with tools that analyze calls after the fact. Winn.ai takes a different approach by focusing on real-time execution rather than retrospective analytics. Key differentiators include:

Proactive, not passive: Instead of just recording and analyzing calls, Winn.ai guides reps in the moment to improve outcomes as conversations happen.
Enterprise focus: The platform is designed for large, complex sales teams that need to scale best practices and maintain consistency.
Demonstrated results: Case studies show measurable improvements, such as a 33% win rate increase at Deel and a 98% reduction in admin time at Kaseya.
Expanding use cases: While initially focused on account executives, Winn.ai is now being adopted by sales development, account management, and even non-sales teams like support and HR.

Key takeaways for marketers

Real-time sales support: Winn.ai’s AI assistant helps sales teams apply strategy during live calls, not just in post-call reviews.
Improved data quality: Automated CRM integration means more accurate and complete sales data for marketing analysis.
Scalable consistency: The platform enables organizations to roll out new playbooks and strategies quickly, ensuring all reps stay on message.
Operational efficiency: By reducing manual tasks, Winn.ai allows teams to focus on high-value activities that drive revenue.

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