Winn.ai is helping sellers on calls and bridging the hype gap

If you’re an Iron Man aficionado wishing for a real-life AI sidekick like Jarvis to support your noncrime-fighting life, I’ve got good news: This exists now—sort of. Winn.ai is an agentic assistant that has broken free of your inbox and jumped into your sales calls. It can flag key insights, help automate administrative tasks like summarizing meetings, and update your CRM (which we know you don’t want to).

The company says it helped HR tech platform Deel drive 33% higher sales win rates by reinforcing “Meddicc” (a popular sales qualification methodology that stands for metrics, economic buyer, decision process, decision criteria, identify pain, champion, and competition) in real time. Winn.ai says it also helped IT management software provider Kaseya reduce administrative time by 98% while aligning sales reps.

Here at Revenue Brew, we talk a lot about sellers getting back to selling, and copilots like this have emerged as a one way to potentially reduce the drudgery of administrative work. But can these real-time agents meet the hype and meaningfully drive ROI?

Out: vibe-coding. In: vibe-selling.

What do you call the moment when vibe-coded solutions become real-time augmented conversations? If you ask Winn.ai co-founder, Eldad Postan-Koren, he would say that is “vibe-selling.” “We believe the only effective way to change people’s behavior is with real-time guidance,” said Postan-Koren.

He compared Winn.ai’s impact to that of companies like navigation platform Waze and personal writing assistant Grammarly on their respective fields. 

“We are integrated into the knowledge base of the company,” Postan-Koren said. “During the conversation, someone is being asked about this and that. It could be competitors, it could be technical data, it could be privacy, could be whatever. We know to give the right answer.”

Rather than AI replacing sellers, Postan-Koren said he envisions a future where AI augments sellers to make them more effective. He predicted that by 2030 all conversations, not just sales conversations, will be augmented with real-time AI.

“We believe the one-size-fits-all playbook is just a necessity, and everything is going to be personalized,” said Postan-Koren.

AI ride along

Nate Sintros, revenue operations manager at data security company Cyera, said that while his company has been in the midst of a hypergrowth cycle, Winn.ai has helped sales teams grow by ensuring that sales methodologies are maintained.

“Because the AI is capturing qualification data during the conversation, it naturally keeps the rep on track. We’ve actually seen a 20% increase in playbook adoption because it reminds reps of what they need to cover,” Sintros told Revenue Brew in an email.

Another way the AI tool is helping Cyera is by collecting accurate and reliable data. Sintros said his team’s Salesforce fill rate jumped from 44% to almost 90%.

“The real win is that we stopped turning high paid sales reps into expensive data entry clerks. Instead of wasting hours manually filling out fields, they are back on Zoom actually selling Cyera,” Sintros said.

Expert insight: AI deployment

According to Jamie Cleghorn, senior partner at Bain, the start of the year has certainly seen companies consider the ROI of AI deployment. As the value gap surrounding AI investments becomes apparent, companies, especially early adopters, are looking for the next best innovation, and real-time assistants seem to be dominating that trend.

“We’re seeing the early adopters start to do that, and some of the early AI tools that really started as knowledge management, search and discovery, are moving downstream from knowledge management to human enablement,” Cleghorn said.

Not only is Cleghorn seeing increased demand from consumers on that front, he is also seeing a shift in the startup space as new players seek to meet that demand.

“I’m talking to way more startups that are trying to convince me that their stuff’s working than I am talking to clients who are really successfully using AI,” Clegorn said.