Why Sales Enablement is broken and how to fix it

Jul 9

Sales enablement has a performance problem, and Keenan, bestselling author of Gap Selling and Gap Prospecting, thinks he knows why. In a lively, unscripted session, Keenan previewed the core ideas from his forthcoming book, Gap Revenue Performance, arguing that enablement as a function has drifted away from the one thing that actually matters: moving the number.

The 15-Year Reckoning

Keenan opened with a blunt diagnosis. Roughly 15 years ago, before sales enablement became a formal discipline, a much higher share of reps hit quota. Today that number has collapsed. He cited around 63% of sellers attain quota to just 16%, alongside rising deal-stall rates, longer sales cycles, and enablement content that frequently goes unused. Somewhere around 2012–2017, as enablement functions scaled up, the trend lines that should have improved instead went the other way.

His point isn't that enablement professionals are failing individually, it's that the function was built on the wrong foundation.

The Root Cause: L&D DNA in a Performance Job

According to Keenan, the core issue is that enablement teams were staffed and structured using a learning-and-development (L&D) model, borrowed largely from academia. Universities are built to transfer knowledge, not to guarantee real-world performance. When that same mindset shaped sales enablement, teams ended up optimizing for training completions, certifications, and playbooks. The metrics that feel productive - training completion, seller confidence, NPS, etc - don't correlate with revenue outcomes.

He illustrated this with a story about a Fortune 500 prospect whose head of enablement proudly reported "improving numbers," which turned out to mean certification completion rates with no visibility into win rate, average sales price, or cycle time. Keenan says this pattern shows up constantly and enablement leaders can rarely connect their initiatives to actual sales metrics.

From Knowing to Doing to Performing

A recurring theme, sparked by audience member Christine's "know it, say it, sell it" framework, was the gap between understanding a concept and being able to execute it under pressure. Keenan illustrated this with his daughter's experience training as a competitive mogul skier: she has to master a trick in a safe environment (water ramps) before attempting it on snow, and even then she progresses through stages — smooth runs, a few bumps, more bumps, full competition — with coaching feedback at every step.

He mapped this directly onto sales training: knowing isn't doing, and doing isn't performing.

Four Types of Enablement Orgs

Keenan outlined four dysfunctional patterns he sees repeatedly:

Random: Enablement constantly ships new playbooks, tools, and trainings with no connective thread tying activity to outcomes.
Heroic: The CRO parachutes in during the final weeks of the quarter to manually rescue deals, masking a lack of systemic process.
Peacock: The org has beautiful playbooks, polished certifications, and strong training cadence, but nothing connects to actual performance movement. He called this the most dangerous pattern because it feels like success.
Compounding: The implied fourth type, where a real operating system connects skills, opportunity coaching, and forecasting to outcomes.

Building the Operating System

The heart of Keenan's framework is a "revenue operating system" anchored by problem-centric selling. It’s the idea that every buying decision starts with a perceived problem and its cost. From there, he laid out four layers:

Skills layer — teaching and certifying what reps need to know (product knowledge, business acumen, problem identification).
Opportunity layer — real-time coaching during live deals (call reviews, discovery evaluation), which he said is where most orgs are weakest.
Manager layer — training frontline managers as "linchpins" who evaluate deals against a shared methodology using an observe-describe-prescribe approach.
Forecasting layer — using forecast accuracy as the ultimate proof point of performance.

He also introduced the concept of a Problem Identification Chart (PIC) — a short list (often just three to five) of core business problems a company's product actually solves, broken into root causes and impacts and distinguished between active reinforcement (role plays, coaching) and passive reinforcement (building workflows, like proposal templates, that force reps to apply what they were taught in order to do their jobs at all).

Key Takeaway

Keenan's central message: enablement needs to stop measuring itself by activity and start building a connected system that ties skill-building to live coaching to measurable revenue outcomes. Without that connective tissue, even the best-resourced enablement teams risk becoming "peacocks": impressive on paper, invisible in the numbers.

Keenan's new book, Gap Revenue Performance, expands on all of these frameworks, including a self-assessment to identify which of the four organizational types best describes your team.