Gap Selling Author, Keenan Reveals Why Your Sales Enablement is Broken

In this episode of the SaaS Sales Performance Podcast, we were joined by none other than Keenan the author of the bestselling book Gap Selling and CEO of A Sales Growth Company — for an unfiltered conversation about what’s really going wrong with sales enablement today.

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The Harsh Truth: Enablement Has Become Too Comfortable

Keenan didn’t sugar-coat it.

“Enablement’s become school. Everyone’s tracking course completions and certifications — but nobody’s tracking if it’s actually helping close more deals.”

According to Keenan, too many enablement teams have defaulted to learning and development-style initiatives. Lots of content, lots of courses, very little connection to results.

And that’s a serious problem.

Because when budget cuts come around, as they have for many sales teams over the past 18 months enablement is often first on the chopping block. Why? Because leadership can’t see the value.

The Core Problem: No Line of Sight to Revenue Metrics

Keenan laid it out clearly. Enablement often can’t answer basic questions like:

• What’s our current win rate?
• What’s the average sales cycle length?
• Has average contract value increased or decreased since we rolled out training?
• How many reps are consistently hitting quota?

Without a direct link between enablement efforts and key revenue metrics, the function gets viewed as “nice to have” — not mission-critical. And that, Keenan argues, is the real reason we’re seeing enablement teams being cut or deprioritised across the industry.

The Opportunity: Rebuilding Enablement as a Business Growth Engine

Despite the critique, Keenan remains bullish on the role enablement could play — if it steps up.

Drawing a powerful comparison to elite sports, he explained:

“In professional sport, performance coaching is about improving what happens on the pitch — not just in the gym. The same has to apply in sales. Enablement should exist to make the team win more. Period.”

Introducing the SPEED Model

To fix the problem, Keenan’s company built the SPEED Model, a strategic framework for operationalising enablement around business impact. It stands for:

• Skills Management: The foundational training layer. Yes, this matters — but it’s only the beginning.
• Performance Execution: The in-field application of those skills — this is the opportunity management layer.
• Enablement: The connective tissue that ensures alignment across layers.
• Execution Management: Frontline manager accountability and measurement.
• Delivery: Forecast accuracy and business outcomes.

The Three-Layer Model of Sales Execution

The SPEED model maps across three core layers of revenue performance:

1. Skills Management Layer
   Where enablement traditionally plays — onboarding, playbooks, LMS, certifications. Still important, but only useful if connected to what happens in live deals.
2. Opportunity Management Layer
   This is where the rubber meets the road. Are reps applying what they’ve learned? Are they asking the right questions, positioning effectively, qualifying properly? This is owned by frontline managers — and supported by enablement.
3. Forecast Management Layer
   The output. Deals won. Forecast accuracy. Average deal size. This is where business leaders live, and it's where enablement must now prove its worth.

Where Most Companies Fall Short

Too often, companies focus only on the skills layer — and fail to track whether those skills are being executed in the field. As a result:

• Managers don’t have the tools or frameworks to coach live deals
• Reps aren’t held accountable to behaviour change
• CROs don’t see performance improvement — just more LMS usage
• Forecasts stay unreliable, and revenue becomes unpredictable

As Keenan put it:

“It’s like running drills at practice and never watching game film. You don’t get better by training alone — you get better by applying it under pressure and getting feedback.”

So, What’s the Fix?

Keenan says it starts with treating enablement like a business function, not a support team.

That means:

• Aligning enablement efforts with key sales KPIs: win rate, time to close, average deal size, quota attainment
• Holding enablement accountable to outcomes, not just participation
• Equipping frontline managers to coach based on real deals, not generic theory
• Building feedback loops between performance, coaching, and skill development

It also means using frameworks like SPEED to build clarity across teams. Everyone — from the CRO to the enablement lead to the AE — should understand how skills translate into revenue.

Why This Matters Now

As revenue teams face tighter targets, more scrutiny, and higher pressure to justify spend, the role of enablement is under the spotlight.

But instead of seeing this as a threat, Keenan argues it’s a massive opportunity.

“Enablement was created to solve real performance problems. Somewhere along the way, we lost sight of that. But now’s the time to get back to it.”

If you’re in sales leadership and looking to make enablement a strategic lever — not a sunk cost — this episode is essential listening.

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