By Aaron Melamed, CEO of Itero
Introduction: What Are You Really Doing as a Manager?
A great mentor of mine once said, “You’re either managing people up or managing them out — or else, what the f** are you doing?”* That hit me hard.
At the time, I was deeply process-oriented. My mindset was: faster, more efficient, more scalable. But I wasn’t helping people actually get better. I wasn’t coaching. I was optimizing — without a compass for personal growth.
That changed when I was introduced to the Command of the Message framework. For the first time, I had the language and structure to coach reps beyond surface-level metrics. I learned to see the subtleties in conversations — the missed cues, the opportunities left untouched — and teach others how to spot and act on them.
Years later, I’d built a level of fluency in coaching where I could call out things reps couldn’t see themselves. It was incredibly rewarding.
But now?
I think AI is going to be way better at this than most of us — and soon.
Sales Coaching Is at an Inflection Point
Dharmesh Shah recently wrote about how AI Agents’ capabilities are doubling every seven months (read it here). Just let that sink in.
Imagine where we’ll be in one year.
Sales coaching has always had some messiness — subjective, inconsistent, and usually reactive. The true great sales coach is a rare breed. We’ve relied on sporadic call reviews, anecdotal feedback, and vague “gut feels.” But now, the emergence of AI Sales Coaching means every single call can be scored, analyzed, and coached — objectively and instantly.
The impact is staggering. Managers can get instant access to insights, and start forming opinions before it impacts ARR.
The Broken Feedback Loop (and How AI Fixes It)
Traditionally, the coaching loop looked like this: a rep would start taking calls, managers would listen in early, and eventually release them into the wild. That early stage was intensive — especially with junior reps who were more open to feedback. But once you moved on to other priorities, the calls piled up, feedback slowed down, and the loop broke. Often, months would pass before issues surfaced — either because the rep missed quota or deals consistently stalled. Then began the retroactive scramble: digging into calls, diagnosing problems, giving feedback, and hoping it stuck. It was slow, expensive, and often too late.
The better way is to monitor every single call, using AI to detect patterns that quietly kill deals — like skipping discovery questions or mishandling objections. With Itero, you’re alerted before the close-lost emails stack up. You coach immediately. Then AI watches future calls to confirm the rep is applying the fix. The loop tightens. Performance improves. And reps grow faster — without months of missed revenue.
Playbook Adherence = Higher Win Rates
There is a reason why we use playbooks. “Nail it, then scale it” as another mentor of mine would always say. When we truly do this, and the companies that have (MongoDB, Snowflake, to name a few), you see higher win rates.
Monitoring adherence is very difficult without AI. That’s why there is a need for training and enforcement plans, and the amount of money we spend on that is crazy.
This isn’t about replacing human managers — it’s about empowering them.
When every rep gets structured, unbiased, and methodologically aligned feedback after every call, your win rates improve. Not in theory — in reality.
We’ve seen teams using Itero hit:
- 2x faster skill development for new reps
- 40% higher adherence to methodology frameworks
- 111% increase in booked meetings over the phone
- Clear improvements in discovery, objection handling, and storytelling
And sales leaders? They get dashboards showing where the team is strong, where they’re weak, and exactly who needs help with what.
How Itero Is Leading the Way
At Itero, we’ve built a platform that fundamentally reshapes how coaching happens — not by adding more to managers’ plates, but by embedding intelligent feedback loops directly into the sales process. Every call is automatically scored by AI agents trained on your specific sales methodologies, like MEDDPICC or SPIN. The feedback is grounded in your actual playbooks, buyer personas, and product knowledge, so reps get coaching that’s relevant and tactical — not generic. When a skill gap is identified, Itero doesn’t just flag it — it recommends precise coaching actions and tracks whether those improvements are sticking. Reps can also simulate real scenarios using past calls or customized buyer personas, honing the skills that matter most. And for managers? They get crystal-clear visibility into which reps are improving, where they’re struggling, and how coaching is impacting win rates. It’s consistent, contextual, and completely scalable — finally, a coaching system that works as hard as your team does.
Final Thought: Coach Up, or Get Left Behind
AI isn’t the future of sales coaching — it’s the present. And if you’re still relying on tribal knowledge and sporadic reviews, you’re already behind.
The best managers will embrace this shift. They’ll use AI to coach up their teams with precision.
