I’m sitting in my office running the AI Sales Summit as Eldad Postan-Koren, CEO and co-founder of WINN.AI, takes the stage—beaming in from Tel Aviv—and within minutes he reframes a problem every sales leader knows too well: Why don’t my reps listen to me? He isn’t talking about insubordination; he’s talking about inconsistency—the missed prep, the shallow discovery, the empty CRM fields, the follow-ups that never go out. We’ve all tried the band-aids: mandatory fields, more training, more meetings. Eldad calls it what it is—an illusion of compliance that adds friction to the workflow without changing behavior.
Then he makes a move I love: he zooms out beyond sales to human nature. If people struggle to take a single pill once a day, why do we expect perfect adherence to a complex playbook? Consistency is hardwired against us. If you want change, you need real-time help at the moment of action. Not post-mortems after a deal is lost guidance while the call is happening.
Eldad’s metaphor lands; Waze didn’t invent maps; it made navigation live. Grammarly didn’t invent writing; it made editing present to the writer. GitHub Copilot didn’t invent programming; it made expertise ambient for the coder. In the same way, sales won’t be transformed by more dashboards—it will be transformed by real-time augmentation that sits beside the rep during the conversation.
That’s the heart of WINN.AI’s thesis and what Eldad calls vibe selling. He breaks it into five live layers:
- Efficiency: meeting prep, CRM updates, and follow-ups handled in the flow—five minutes before, during, and five minutes after the call—so reps become “superhuman” on the basics that used to slip.
- Process adherence: the right-side panel that quietly enforces your discovery/negotiation checklist in real time—what’s covered, what’s weak, what’s missing—so the playbook stops being a PDF and becomes a companion.
- Instant expertise: as if your best solutions engineer and product marketer are whispering in your ear—on security, competition, pricing—so “I’ll get back to you” becomes the exception, not the reflex.
- Live coaching: prompts to sharpen objection handling and close with confidence—while the buyer is still with you.
- Manager visibility: call-level insights flowing upward so frontline leaders and executives can coach better, promote smarter, and—yes—reassign when needed, based on what actually happens on calls.
Eldad also looks five years out and makes three predictions I find compelling. First, every professional interaction will be AI-augmented; sales is just the tip of the spear. Second, the generic playbook dies—personalization becomes king because AI can tailor guidance to the rep, the role, the deal, the moment. Third, AI becomes both the active layer of work and the system of record—changing how we think about tools like CRM altogether. In that world, consistency isn’t a slogan; it’s a capability teams perform every day.
What I appreciate is that Eldad refuses the “more platforms will save us” myth. If your core motion is broken, stacking another portal on top won’t fix it. Real-time is the only credible lever for behavior change because it reduces effort precisely when the brain is overloaded—during the live buyer exchange. That’s where trust is won or lost.
Two practical notes stick with me. First, “real time” spans a tight window—five minutes before the call, during the call, and five minutes after. That’s when context is fresh, energy is high, and actions are malleable. Second, the economics are accessible: WINN.AI’s pro plan is $69 per seat, which makes piloting this behavior engine a low-friction decision for most teams.
As the session closes, I’m reminded of a pattern I’ve seen for decades, the tools that endure are the ones that make us better in the moment. Revenue intelligence helps us analyze after the fact; real-time AI helps us perform when it counts. Vibe selling is not a slogan—it’s a shift from retrospective management to live execution. If you want consistency, bring the coach onto the field.
Today’s takeaway from Eldad’s keynote is simple and urgent, don’t wait for the QBR to fix what went wrong. Put guidance where the game is played—on the call. That’s how you turn potential into performance, at scale, and win more—one conversation at a time.
To learn more, visit: http://www@winn.ai.
Today’s post is by Gerhard Gschwandtner, Founder and CEO of Selling Power.
