WINN.AI Raises $18mn Series A to Guide Sales Reps Live on Calls

TEL AVIV: WINN.AI raised $18 million in a Series A round Wednesday to expand its real-time AI sales assistant that coaches sales representatives during live customer calls, bringing total funding to $35 million since its 2022 founding.

Insight Partners, Mangusta Capital, and S Capital co-led the round with participation from Moneta, HighSage, Alumni Ventures, Sarona Ventures, and OurCrowd.

The Tel Aviv-based startup positions itself against traditional sales analytics tools focused on post-call analysis.

The platform listens during live calls, identifies objections and technical questions in real time, and surfaces answers from the company’s knowledge base while automatically capturing CRM data without manual entry.

Enterprise customers report measurable results. HR-tech company Deel saw win rates jump 33% after five months. Data security startup Cyera doubled its CRM fill rate and increased playbook adoption by 20%. IT management firm Kaseya synchronized 1,200 sales reps and reduced administrative time by 98%.

WINN.AI tripled annual recurring revenue in 2025, grew 30-fold over two years, and maintains a 0% churn rate among enterprise clients including Intercom, WalkMe, and Snyk.

The company employs 40 people across Israel and the United States. New capital will accelerate U.S. market expansion and grow the Israel development center. WINN.AI is also expanding beyond account executives into sales development, account management, solutions engineering, customer success, and HR teams.

AI-related sales and marketing startups raised nearly $4 billion in venture capital in 2025, up from $3.4 billion in 2024.