In this episode of Coach to Scale, we sit down with Sriharsha “Sai” Guduguntla, co-founder of Hyperbound, to unpack one of the most pressing challenges in revenue leadership: the coaching crisis. Despite billions invested in enablement tools, most frontline managers still spend less than 5% of their time actually coaching, and it’s costing teams deals, confidence, and retention. Sai shares how Hyperbound is redefining sales practice by enabling reps to roleplay high-stakes calls, objections, and negotiations using AI before they ever speak to a real prospect.
Sai and host Matt Benelli explore why traditional training doesn’t stick, how to coach the iPhone generation, and why AI-driven feedback is the key to scalable performance improvement. From building reps’ confidence to reducing CAC, shortening ramp time, and even coaching managers themselves, this conversation delivers practical insight for CROs and GTM leaders committed to leveling up their teams. If you think having Gong means you’re coaching, think again.
Let me ask you something I’ve asked dozens maybe hundreds of revenue leaders over the years:
What’s the one thing you wish your managers did more of?
Nine times out of ten, the answer is the same:
“I wish they spent more time coaching.”
In this week’s episode of Coach to Scale, I sat down with Sriharsha “Sai” Guduguntla, the co-founder of Hyperbound, an AI-powered roleplay platform changing the way sales teams practice. And if you lead a go-to-market team, you need to hear what he has to say.
Because here’s the truth: coaching is broken in most sales orgs and it’s not just your reps who are underperforming. The tools we’ve invested in are gathering dust. We’re paying for Pelotons, but no one’s riding them.
Coaching ≠ Call Listening
Sai and his co-founder, Atul, have done 2,000+ user interviews. What they found isn’t surprising, but it is alarming: most sales managers spend less than 5% of their time coaching. And 60% of them openly admit it.
Yes, you might have Gong. But let’s stop pretending that means your managers are coaching. It’s like buying a gym membership and thinking that alone builds muscle.
It doesn’t.
Practice Before You Play
Hyperbound was born from necessity. Two technical founders with zero sales experience found themselves in front of enterprise buyers and failing. So they did what engineers do: they built a tool to simulate practice calls.
That tool became Hyperbound.
And that’s where the real lightbulb moment happened:
Reps shouldn’t be practicing in the game.
Think about it. Would you send a quarterback onto the field without running plays first? Then why are your reps practicing on your prospects?
With AI roleplay, reps can now rehearse tough objections, test talk tracks, and refine delivery before the big call. It’s deliberate practice that mirrors real scenarios, with instant feedback. No more waiting weeks for a 1-on-1.
Why Training Doesn’t Stick
You know those expensive SKOs and training programs? The ones that cost you seven figures and make your enablement team feel good?
87% of that content is forgotten within a month.
It’s not that your team’s lazy. It’s that retention doesn’t come from a two-day offsite. It comes from ongoing, contextual practice the kind that Hyperbound enables.
Reps now have a way to keep learning all year long, and you can measure how much they’ve retained. That’s the difference between enablement that feels good and enablement that actually works.
Data Over Drama
One of my favorite parts of the conversation was how Sai explained the power of objective, AI-driven coaching. AI doesn’t care who you are. It’s not biased by personality or favoritism.
And most importantly, it gives your reps something they can’t argue with: data.
If your best rep isn’t asking for permission on cold calls or skipping social proof on demos, the AI will call it out. Not because it’s being critical, but because that behavior deviates from what success looks like across your org.
Reps can’t improve what they can’t see. And managers? They’re no longer guessing. They’re coaching with evidence.
Your Managers Need Coaching, Too
Here’s something that might sting: your managers might be worse at coaching than your reps are at selling.
Why? Because no one taught them. We take high-performing reps, hand them a team, and wish them luck.
Sai’s team is building tools to coach managers, too, letting them practice coaching conversations with AI-replicated reps. It’s meta, yes. But it’s exactly what we need to scale quality coaching across the org.
Not Everyone Is Ready
A CRO once told Sai: “If it’s a confidence problem, why not just give everyone a shot of whiskey in the morning?”
Dead serious.
The truth is, not every company is ready to invest in actual enablement. And Hyperbound doesn’t try to serve those orgs, and neither should you.
If you’re a CRO who believes in coaching, in performance, and in building a culture where reps can improve every day this episode is for you.
Listen to the Full Episode
And Try Hyperbound for yourself: https://hyperbound.ai
And if you’re ready to coach ’em if you want to keep ’em, you know where to find us.
