Why CROs Can’t Rely on Training and Tools Alone Anymore

The case for a Problem-Centric Operating System in Sales

Despite record investments in sales enablement, technology, and training, the numbers are going in the wrong direction.

• Win rates are down 18%.

• Sales cycles are 16% longer.

• Average deal values have fallen 21%.

• 73% of sellers missed quota last year—even after companies lowered quotas by nearly 20%.

Those aren’t outliers; they’re the benchmark data (Ebsta 2024 B2B Sales Report). Layer in Gartner’s warning that 72% of sellers feel overwhelmed by required tools and skills, and Forrester’s prediction that more than half of enterprise deals will shift to digital self-serve by 2025, and it’s clear: the modern revenue engine isn’t just underperforming—it’s misfiring.

Why This Keeps Happening

CROs have treated sales performance like a plumbing problem. Buy more tools, bolt on more training, increase activity, patch forecasting with AI, and hope it all flows together. But the results prove otherwise. Tools don’t talk to each other. Training doesn’t stick. Managers still don’t know which deals will close.

The deeper issue? There’s no operating system that ties it all together. Revenue organizations run on disconnected apps, disjointed processes, and individual manager preferences. That’s why forecasts remain unreliable, pipeline quality is inconsistent, and sellers are stretched to exhaustion.

The CRO’s Dilemma

CROs today face a paradox:

• You’re being asked to deliver predictable revenue growth in an environment where predictability is collapsing.

• You’re expected to improve win rates while buyers do more research alone and sellers are invited into fewer deals.

• You need to deliver shorter cycles and higher ACV, but the average rep spends more time navigating internal systems than selling.

No tool or training program can fix this on its own. Because the real issue isn’t execution—it’s the absence of a system that makes execution coherent.

ASG Problem Identification O:S

The ASG Problem Centric Operating System ensures sales investments in tools, and training actually deliver.

The Missing Piece: A Problem-Centric OS

What sales lacks—and what CROs need—is a Problem-Centric Operating System (OS).

Unlike a methodology or another point solution, a Problem-Centric OS acts as the logic layer that connects training, tools, and forecasting into a unified whole. It forces the entire revenue organization to operate from the buyer’s problem backward, not the product forward.

Here’s what changes when CROs run on a Problem-Centric OS:

• Forecast accuracy improves because deals are inspected through the lens of whether the buyer has real clarity, control, consensus, and confidence to change—not just whether reps filled out MEDDIC or updated a CRM field.

• Win rates increase because reps are diagnosing the right business problems, not pitching features. (Ebsta’s top 31% of sellers who consistently exceed quota all share this discipline: sharper qualification and tighter alignment to buyer pain.)

• Sales velocity accelerates because the system reduces friction—teams stop reinventing discovery, coaching, and deal inspection every time.

• Enablement becomes stickier because reps aren’t just trained once; they’re reinforced daily inside a system that requires them to work problem-first.

What CROs Get Wrong

The instinct is to keep doubling down on what’s familiar: more training, more dashboards, more tools. But that’s like replacing the tires on a car with no transmission. You can spend millions, but you’ll never move faster.

CROs who want to escape the cycle have to start asking: What operating system is my revenue team actually running on? If the answer is a patchwork of methodologies, disconnected enablement programs, and inconsistent manager coaching, the outcomes won’t change.

The Takeaway for CROs

The state of sales today is not the fault of your people. It’s the fault of a system that doesn’t function as a system.

The CROs who win the next five years won’t be the ones who buy the most technology or run the most training sessions. They’ll be the ones who implement an operating system for revenue—a system designed around buyer problems, embedded across sales process, enablement, deal management, and forecasting.

Because until sales runs on a real OS, it will remain what it is today: a collection of parts, but not a machine.