February 16, 2026
A Growing Market: Real-Time AI Coaching for Customer Reps
The real-time AI coaching marketplace for customer support agents continues to accelerate, with WINN.AI being one of the latest platforms to secure fresh investment to fuel its expansion.
The Tel Aviv-based company has now raised $18 million in Series A funding, which it plans to use to scale operations in the United States and continue developing its product capabilities. Demand appears to be strong. Launched in June 2023, the company reported triple annual recurring revenue for 2025 and thirty times growth over the past two years, while maintaining zero churn among enterprise customers.
Changing Outcomes in Real-Time
WINN.AI integrates directly with enterprise CRM and business intelligence systems including Salesforce and HubSpot, enabling sales teams to receive contextual prompts and structured guidance during live interactions. The company says this approach improves win rates, operational efficiency and adherence to sales playbooks. One if its customers, Deel, for example, reported a 33 percent increase in win rates after five months of use if its platform.
It appears to be a recipe for success. Describing what makes the company different, WINN.AI’s CEO, Eldad Postan-Koren, said: “We don’t analyse the past; we shape the present. By guiding execution in real-time, we change the outcome while the customer is still on the call.”
The Emerging Competitive Landscape
While WINN.AI may offer a unique approach in specific areas, the technology in a broader sense is not itself original, though still relatively new. Call recording and performance analytics tools have existed for years, but since the post-2022 AI explosion, live coaching and decision-support have rapidly become a popular supplement to these CX tools. This is unsurprising given that more than half of leaders are prioritising AI for greater CX efficiency. A few names to have already established themselves within the sector include Clari, Observe.AI, and Balto.
Clari: The largest of these companies, Clari, has its own conversation intelligence and live coaching solution, ‘Clari Copilot’. It provides real-time insights and post-call analysis to support deal execution, forecasting accuracy, and customer representative performance. The product is part of Clari’s broader revenue platform, which connects sales engagement, forecasting, and execution data in one system. Clari asserts its Copilot can standardise winning behaviours across teams by turning customer conversations into structured revenue intelligence.
Observe.AI: Widely deployed by large contact centres within the vertical, Observe.AI provides AI-driven conversation intelligence and agent performance tools. Its platform analyses voice and chat interaction to deliver real-time guidance, quality assurance automation, and coaching recommendations. As with Clari, which has received around half a billion dollars in funding so far, Observe.AI has also raised over $214 million, according to Latka’s company information database.
Balto: Relatively smaller but still a well-known player within the technology niche, serving roughly 3,200 customers, is Balto. Balto also offers real-time AI guidance for contact centre agents during live customer conversations. The platform listens to calls as they happen and provides prompts, coaching tips, and recommended responses to help agents follow best practices. It can integrate with major contact centre and telephony systems so teams can deploy live coaching directly into existing workflows.
Live AI Coaching Enters CX Mainstream
The rise in real-time AI coaching reflects a structural shift across the customer experience technology landscape. Organisations are investing heavily in tools that move intelligence from retrospective analysis into live decision support, driven by advances in generative AI, speech recognition, and workflow integration. That is, if humans are involved at all in the process. NiCE data recently showed that AI-handled enquiries have increased 77 percent year-over-year. These days, if AI is not part of a customer service interaction, it is likely performing the task on its own.
