Sales Coaching Challenges: Why AI Matters Now
Every sales leader, RevOps partner, and frontline manager shares the same ambition: help their teams win more. But on the ground, the story often looks different.
A deal stalls because a rep missed a subtle buying signal. A new hire struggles through their first quarter, unsure how to handle objections. A frontline manager wants to coach more, but back-to-back meetings and pipeline fire drills leave little time for meaningful feedback.
The result? Coaching quality is inconsistent, pipelines slip without timely guidance, and sellers ramp slower than anyone would like.
These gaps are exactly where AI can step in. On the Hyperengage Podcast, Ioanna Onasi, CEO of Dextego, unpacked five practical ways AI can transform coaching from a sporadic, reactive task into a consistent driver of performance.
1) Influence: The Missing KPI
“Although we had very good learning opportunities in terms of online courses and playbooks, the results were not there. Not because they were not saying the right thing, but because they didn't have those soft skills that truly move the needle, especially today. The one KPI that is missing because it's hard to measure and develop is influence.” — Ioanna Onasi
In sales, scripts don’t close deals — influence does. Influence is that blend of trust, empathy, and clarity that gets prospects to act, not just listen. The challenge? It’s notoriously hard to measure and develop.
AI now makes it possible to coach influence: surfacing how a rep sounds, not just what they say. Teams can review tone, pacing, and presence in objection handling, highlight soft-skill wins in huddles, and track real outcomes like call-to-next-meeting rates. When influence goes up, second meetings follow.
2) Real-Time Coaching Beats Recaps
“People think reviewing a call after the fact is coaching, which it’s not. That’s the worst thing you can do. It's like us watching a recorded game and telling you, 'hey, you should have passed the ball there.' Well, it's too late; the game is done.” — Ioanna Onasi
Think about sports: no coach waits until after the championship to tell the team what they should have done. Yet in sales, that’s often the default.
Real impact happens before, during, and right after the game — in this case, the call. AI can prep reps with objection cues, whisper reminders in live conversations, and deliver same-day insights while details are fresh. Even a 15-minute rehearsal before a key meeting can flip the outcome. Track the numbers and you’ll see the pattern: deals coached in real time close more often than those left for end-of-quarter reviews.
3) Every Seller Deserves a Coach
“Dextego fills the gap of coaching for sales leaders who can’t be everywhere at once.” — Ioanna Onasi
Coaching shouldn’t be reserved for top performers or squeaky wheels. Every rep deserves support — even at 10 p.m. before a big pitch, or five minutes before their first discovery call.
That’s the promise of AI coaching: always-on, personalized guidance rooted in CRM data, playbooks, and product context. It ensures consistency too — every seller gets reinforced on the same methodology, regardless of which manager they report to.
The payoff? New hires ramp faster. Time to first deal shrinks. And with Dextego learning from your best reps and scaling their expertise, the whole team levels up.
4) Coach the Coaches
“When someone leaves the company, 80% of the reason why they left has to do with their relationship with a manager. We hire someone and make them a manager because they were good at their job, but that doesn't mean they are good managers. So, it's not that we're replacing anyone, but we're amplifying the impact they can have so that our productivity and engagement goes up.” — Ioanna Onasi
Here’s the truth: most frontline managers were never trained to coach. They were top sellers promoted into leadership. But managing is a different game.
AI helps amplify their impact. By surfacing the right focus points for each rep, providing data-driven coaching prompts, and reinforcing empathy and feedback skills, managers can turn scattered 1:1s into structured, growth-focused sessions. Add a simple peer-coaching circle or a bootcamp, and suddenly managers aren’t just keeping teams afloat — they’re building loyalty and capability. The numbers back it: teams with strong coaching see far lower attrition.
5) Measure and Improve Continuously
“I truly believe anyone can develop skills no matter their age, no matter their background. Neuroplasticity is there to tell us that we can indeed change the way we're wired.” — Ioanna Onasi
Sales coaching isn’t one-and-done. It’s a habit. AI makes it measurable.
Pick one skill each quarter — say, asking open-ended questions. Baseline it, coach around it, and rescore at month’s end. Share the improvement trend with the team so progress is visible. When people see they’re improving, they double down. Over time, coaching turns into a growth engine, not just a checkbox.
Conclusion
AI coaching isn’t here to replace managers. It’s here to amplify them. Every seller gains access to timely, personalized feedback. Managers get clearer signals and more time to focus on impact. Leaders see consistency and lift across the board.
The future of coaching is continuous, measurable, and available to everyone — and with AI, that future starts now.
