The Silent Struggle of Leading a Sales Team:
Graycommit Problem Space
15 min read . Sep 28,2024
Sales Challenges
Agent Engine
Being a VP of Sales is not what you thought it would be.
You didn’t sign up to be the chief firefighter, constantly putting out flames across your team. But here you are—day in, day out—dealing with missed targets, lost deals, and a group of AEs who seem to be spinning their wheels. You’ve tried everything. You’ve run every playbook in the book. You’ve implemented CRM systems, held endless training sessions, brought in motivational speakers, and revamped your processes more times than you can count. But despite all of it, it feels like your sales team is stuck in quicksand.
Every solution seems to be a temporary band-aid. The problems keep coming back, deeper, stronger, more frustrating.
The Burden of the CRM That Was Supposed to Fix issues
You remember when you rolled out your new CRM. It was a big investment, but the promise was there: automation, better visibility, and streamlined processes. Everything was supposed to change. Finally, you’d have full insight into every deal, every conversation, every touchpoint. No more guessing about why deals were slipping. No more unclear forecasts.
But here’s the reality now, CRM fancy naming for the system of records!
Your team spends more time inside that CRM than on the phone with prospects. You walk the sales floor, and instead of hearing the hum of conversations, you see your AEs toggling between screens, typing furiously, updating fields. They look more like data entry clerks than the high-energy closers they’re supposed to be.
And what’s worse? Despite all those hours spent updating the CRM, deals still fall through. Opportunities are still missed. And you’re left wondering why, after all this investment, the CRM feels more like a weight around your team's neck than the solution you hoped for.
You tried to fix the problem, but instead, you’ve just traded one frustration for another.
The Endless Cycle of Training
You thought more training was the answer. After all, every AE could always use a little sharpening of their skills, right?
So you scheduled more workshops. You brought in the best sales coaches. You drilled your team on objection handling, on closing techniques, on perfecting their pitches.
But let’s be honest—how much of it actually sticks?
You’ve seen it time and time again. The day after training, your team is fired up. They’re confident. They’re ready. You feel like the investment paid off. But fast-forward a few weeks, and everything starts to look… exactly the same. The enthusiasm fades. The old habits creep back in. Calls still end with “I’ll think about it.” Deals still drag on for months without closing. Prospects still disappear without a trace after that first call.
You invested time, money, and energy into making your team better. But here you are, weeks later, and it’s like nothing ever changed.
The Never-Ending Problem of Follow-Up Failures
You can’t count how many times you’ve heard it: “I forgot to follow up.”
Your AEs know the importance of follow-up. You’ve hammered it into their heads from day one. But no matter how many reminders you send, no matter how many follow-up templates you give them, it’s always the same story. Great discovery calls happen, the prospect is engaged, and then… nothing. The lead goes cold, forgotten in a sea of new meetings and urgent tasks.
It’s maddening.
And what’s even worse is that you know deep down this is killing deals. The deals that could’ve closed, the prospects that could’ve been lifelong customers, are slipping through your fingers because someone didn’t send a follow-up email or make that second call.
You’ve tried to build reminders into your processes. You’ve even tried automating follow-ups. But somehow, the human element—the care, the persistence, the attention—still gets lost. You wonder how many deals are going cold because of simple, avoidable follow-up failures.
The Quota Pressure That’s Destroying Relationships
Your team is constantly under pressure to hit their numbers. You feel it, too. It’s part of the game. Sales is a numbers-driven business. But lately, you’re starting to feel like the pressure is doing more harm than good.
Your AEs are pushing too hard. You can hear it on their calls. They’re rushing prospects, focusing more on closing the deal than understanding what the prospect really needs. They’re jumping to solutions before even listening to the full problem. They’re offering discounts too early, hoping it’ll push the prospect over the edge. And when that doesn’t work, they get desperate. You’ve seen it happen: AEs calling the same prospect three times in a day, hoping that persistence will somehow win the deal.
But it’s not winning. It’s driving prospects away.
The worst part? You understand why it’s happening. Your AEs are panicking. They’re staring down their quotas, they’re looking at the end of the quarter, and they’re scrambling. But in their rush to meet their numbers, they’re burning bridges. They’re killing deals that could’ve closed—maybe not this quarter, but eventually. And the pressure you put on them? It’s backfiring.
The Script That Became a Crutch
A while back, you decided to introduce call scripts. It made sense. Consistency is key, right? If every AE follows the same script, you should see more predictable outcomes.
But now, when you listen to calls, something’s off.
The conversations sound… robotic. Your AEs are following the script to the letter, but it’s like they’re on autopilot. They’re not listening. They’re not adapting. They’re just going through the motions, checking off boxes, waiting for the prospect to say something that matches a pre-written response.
And the prospects? They can feel it. You can hear it in their voices—the hesitation, the disconnection, the polite “we’ll get back to you.”
It’s clear. The script that was supposed to streamline your sales process has turned into a crutch, stripping your AEs of their ability to engage with prospects as humans. And once again, you’re left wondering why something that was supposed to help is now doing the opposite.
The Burnout You Can’t Ignore
One of your top AEs, Rebecca, has always been a high performer. She’s the one you could count on to hit her numbers, to close big deals, to lead by example. But lately, something’s changed.
She looks tired. She’s snapping at her teammates. Her deals, once smooth and easy, are starting to stall. You’ve overheard her on calls—where she used to be sharp and persuasive, she’s now impatient and brusque. The charm that once won her deals is fading.
You know what this is. She’s burned out.
The constant pressure, the endless calls, the overwhelming admin work—it’s all catching up to her. And the worst part? You don’t know how to help her. Because the truth is, Rebecca’s not the only one. Your whole team is feeling it. The exhaustion, the grind, the never-ending cycle of targets and deals and follow-ups—it’s wearing them down.
And you know that if you don’t find a way to fix it, you’re going to lose more than just deals. You’re going to lose your people.
The Meetings That Go Nowhere
How many meetings have you sat through where it feels like everyone’s talking, but nothing’s getting done?
You’ve held pipeline reviews, strategy sessions, team check-ins. You’ve spent hours analyzing data, going over the numbers, dissecting deals that went wrong. And yet, despite all of it, the same problems keep coming back. The same deals keep slipping through. The same objections keep coming up.
You’ve tried to get to the root of it. You’ve asked your team what they need, where they’re struggling. But the answers are always vague. It’s like no one can really put their finger on what’s wrong—and yet, everything feels wrong.
And so the meetings continue. The hours tick by. And by the end of it, you’re left with nothing but a vague sense of frustration and a nagging feeling that you’re not getting any closer to solving the real problem.
The Disconnect Between You and Your Team
Here’s the truth that keeps you up at night.
You don’t know what’s really happening on the sales floor anymore.
You’re supposed to be the leader, the one who drives strategy, the one who steers the ship. But lately, it feels like you’re flying blind. You don’t know which deals are actually close to closing and which are dead in the water. You don’t know how your AEs are handling objections, or if they’re even handling them at all.
You want to trust your team, but the numbers don’t lie. Something’s broken. And despite all the systems, the processes, the tools you’ve put in place, you’re struggling to get a clear picture of what’s really going on.
It’s like there’s a wall between you and your team, and no matter how hard you try to break through, you’re left feeling disconnected, frustrated, and in the dark.
When All Else Fails, What’s Left?
You’ve tried it all. The CRMs, the training, the scripts, the motivational speeches, the team-building exercises, the one-on-ones. You’ve pushed your team, you’ve supported them, you’ve given them every tool you thought they needed to succeed.
We’re not here to promise that we’ll fix every challenge you face as a Sales leader. But we do believe there’s a real opportunity to close the gap between your top performer and the rest of your team using today’s advancements in technology.
With real-time, on-call suggestions, we can guide AEs through the tough moments with prospects, helping them respond naturally and effectively in the heat of the moment. That’s where we start—making their conversations sharper and more confident. Once we prove our value there, we’ll tackle the admin work that bogs them down.
Our vision is simple: let your AEs focus on what matters—building relationships and closing deals. We’ll take care of the rest.
These are my observations after talking to around
230+ Sales Leaders across US & India
Close Right Deals
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