Is Sales Enablement the Next Function to Lose the CEO's Confidence?

Companies have spent years building better-equipped sellers. Before approving the 2027 enablement budget, CEOs should ask whether they have been improving the right part of the revenue system.

There is a pattern CEOs have seen before. A corporate function becomes more sophisticated, its technology stack expands, professional associations establish standards, certifications multiply, and increasingly specialized teams are built to improve performance. Eventually, however, the CEO asks a much simpler question: What business outcome are we getting for the investment?

Marketing knows this question well. HR continues to confront it as CHROs work to establish a clearer connection between workforce strategy and enterprise performance, and revenue leaders increasingly face the same scrutiny as CEOs demand greater predictability from the commercial organization. Sales and Revenue Enablement should assume its turn is coming.

That does not mean enablement is failing, nor does it suggest that training, coaching, methodologies, content or technology no longer matter. There are outstanding enablement organizations producing measurable improvements in seller performance. The more important question heading into 2027 is whether the traditional mandate of enablement remains large enough for the commercial problem CEOs now need it to solve.

For years, companies have invested heavily in helping sellers perform better once they have an opportunity. Sellers have been trained, coached, equipped with methodologies, surrounded by content, given increasingly sophisticated technology and, more recently, provided with an expanding collection of AI tools. Much of this investment has improved seller readiness.

But what happens if the seller is already late? That question should sit at the center of the 2027 enablement conversation.

We Have Invested Heavily in Making Sellers Better

The scale of corporate capability investment is significant. According to Training magazine's 2025 Training Industry Report, U.S. organizations spent approximately $102.8 billion on employee training, an increase of 4.9% from the previous year. Spending on outside training products and services increased 29% to approximately $16 billion, while average spending reached $874 per learner.

Those numbers represent corporate training broadly and should not be confused with sales-training expenditure alone. Sales organizations, however, participate significantly in that investment, and training represents only part of the total commercial capability expenditure. Association for Talent Development research has previously found median sales-training investment of between $1,000 and $1,499 per salesperson, before accounting for the technology infrastructure that now surrounds modern sales organizations.

Consider what has been added to the commercial stack over the past decade: CRM, sales engagement, conversation intelligence, intent data, content management, learning platforms, revenue intelligence, coaching technology, digital sales rooms and increasingly sophisticated AI capabilities for prospecting, role-play, call analysis, account research and content generation. There has probably never been a generation of B2B sellers with more technology, information and resources available to them.

That makes it reasonable for a CEO to ask what commercial capability all of this investment has actually purchased. Faster onboarding, increased content utilization, methodology certification, higher platform adoption and improved training completion may all be useful operating measures, but they do not tell the CEO whether the company has become more difficult to compete against.

The enablement industry's own research suggests there is reason to examine that distinction. Sales Enablement Collective reported that only 43.8% of enablement professionals say they are aligned with senior leadership on the metrics used to evaluate their function. More recent research from the organization says 61.2% of enablement teams identify proving revenue impact as the hardest part of their role.

I do not read those findings as an indictment of enablement professionals. I read them as a governance warning. When more than half of a function is not aligned with senior leadership on how its success should be measured, the first question should not be whether the people are performing. The more important question is whether the enterprise has given the function the right mandate and established the right accountability for it.

The Warning Is Already Coming From Inside the Industry

Highspot's 2025 State of Sales Enablement study surveyed 350 GTM professionals across 21 countries and 61 industries. Only 10% described their organizations as very effective at driving GTM initiatives that deliver business results, while another 35% considered themselves somewhat effective. That leaves 55% struggling to drive those initiatives effectively.

Again, that does not establish that enablement itself is ineffective. Highspot's research also identifies positive relationships between integrated enablement technology, AI-supported coaching and improved commercial outcomes. What the numbers should cause CEOs to question is whether they are dealing solely with a seller-execution problem or with something larger in the commercial operating model.

Much of traditional enablement begins from an entirely reasonable premise: an opportunity exists, and the organization needs to help the seller win it. Training improves the seller's capability. Coaching helps improve execution. Content supports the buyer conversation. Methodologies create consistency. Technology provides information and guidance. Managers inspect and improve opportunities.

Sales Enablement Collective's own 2026 definition reflects much of this historical architecture, describing enablement through coaching, training, content, technology and processes designed to help sellers progress sales opportunities through better interactions with prospects.

There is nothing inherently wrong with that model. The potential problem is where the clock starts: the opportunity already exists. Recent buyer research suggests that may increasingly be too late to serve as the primary starting point for commercial advantage.

What If the Buyer Already Has a Favorite?

Forrester's 2026 Buyers' Journey Survey produced one of the more consequential findings for B2B commercial leaders heading into 2027. The research found that 68% of B2B buyers already have a front-runner vendor in mind at the beginning of their purchasing process, and that vendor wins 80% of the time.

The significance of that finding deserves more attention than another debate about sales methodology or AI productivity. The buyer is not selecting a favorite near the end of the process. In many cases, preference already exists at the beginning of the formal purchasing journey.

Now consider the implications for enablement. A company may have excellent sales training, disciplined managers, an embedded methodology, sophisticated conversation intelligence, AI-generated account briefs, personalized content and rigorous opportunity management. If a competitor became the buyer's preferred supplier several months before that company's seller arrived, much of the enablement infrastructure is now being used to overcome a competitive disadvantage that was established before the traditional sales process began.

This is the distinction CEOs need to understand: seller readiness is not the same thing as market readiness.

Companies have spent years improving their ability to prepare sellers for opportunities. The Forrester research raises a different question: have those same organizations developed an equally sophisticated capability for seeing opportunities while the underlying business conditions are still forming?

Revenue Begins Before the CRM Says It Does

Significant B2B opportunities rarely appear without something changing first. A new executive arrives. Capital is allocated. An acquisition closes. A regulation changes. A facility expansion is announced. A new strategic initiative launches. A technology architecture changes. Hiring accelerates around a new capability. Competitive pressure increases or an operating problem becomes important enough that management can no longer tolerate the status quo.

These events are not necessarily leads, and they should not automatically be treated as buying intent. They are business conditions that may increase the probability that future demand will emerge. The distinction matters because many commercial systems are not designed to mobilize around these conditions.

Instead, the organization frequently becomes active later. An account demonstrates conventional intent, a contact engages with content, an inbound lead appears, an SDR receives a trigger or an opportunity is entered into CRM. At that point Marketing, Sales, RevOps and Enablement begin doing exactly what their operating models were designed to do.

The problem is that the commercial clock may have been running for months.

I describe the gap between when the business condition creating potential demand becomes observable and when the commercial organization recognizes and acts on it as commercial latency. Most CEOs know their pipeline coverage, win rate, average deal size and sales-cycle length. Far fewer know how much commercial latency exists inside their revenue engine.

Going into 2027, they should.

If Forrester is correct that 68% of buyers enter the purchasing process with a front-runner already identified, understanding when and how supplier preference forms becomes at least as important as understanding how efficiently an opportunity moves through CRM.

AI Does Not Automatically Solve the Timing Problem

AI is rapidly becoming the next major enablement investment. Sales Enablement Collective reports that 95.6% of revenue teams are now using AI in some capacity, while 88% of leaders plan to increase their investment. Gartner predicts that organizations using AI-driven sales enablement could achieve 40% faster sales-stage velocity by 2029 than organizations relying on traditional approaches.

Forty percent faster sales-stage velocity would be a meaningful improvement. CEOs should nevertheless ask a simple question before assuming it represents competitive advantage: faster from where?

If the measurement begins at the sales stage, the opportunity has already entered the commercial system. AI can certainly make sellers faster, better prepared and more productive, but none of those improvements automatically makes the organization earlier. An AI-generated account brief may improve the quality of tomorrow's meeting, but it cannot recover the six months during which a competitor was already establishing relationships and influencing the buying organization.

Gartner's own 2026 research reinforces this distinction. The firm found that AI is already saving sellers an average of 4.8 hours per week, yet 72% of sales organizations report low reinvestment of those recovered hours into higher-value selling activities. Gartner appropriately describes the challenge as a systems issue rather than simply a technology problem.

That should be an important warning for CEOs. Organizations can create productivity without creating commercial advantage. There is a very real possibility that some companies will spend heavily in 2027 using AI to make an outdated GTM operating model remarkably efficient.

Efficiency and competitive advantage are not the same thing.

The Enablement Industry Is Beginning to Recognize the Problem

It would be unfair to argue that the major enablement organizations are ignoring these shifts. Some of the industry's own research increasingly acknowledges that the traditional model needs to change.

Gartner described traditional enablement in 2026 as historically operating as a reactive support function and argued for movement toward more integrated, AI-driven, in-workflow execution. Gartner also found that organizations collaborating across sales, marketing and service on enablement content were 2.4 times more likely to achieve strong commercial growth.

Sales Enablement Collective is similarly describing an emerging “Enablement 2.0” model. Its research indicates that 64% of enablement teams now span multiple revenue functions, although only 20.8% describe themselves as truly unified, AI-powered and signal-led. The profession itself is therefore beginning to acknowledge that a function built primarily around training, content and seller support is no longer sufficient.

The concern for CEOs is not that the industry refuses to change. It is that companies can still spend another year buying incremental improvements around the traditional architecture while believing they are transforming it. More coaching, more content, another methodology, another platform, another certification and more AI may each create value, but none automatically answers the larger question: Does this investment materially change our probability of winning?

There Are Two Commercial Problems, Not One

Research from Corporate Visions helps make the distinction clearer. After analyzing more than 150,000 B2B purchase decisions, the company found that 53% of deals recorded as losses were considered winnable but were lost because of preventable sales-process mistakes. Separate 2026 research conducted with Florida State University's Sales Institute examined more than 4,000 B2B sales pursuits and found that the pursuit strategy sellers used most frequently also generated the lowest win rate among the approaches studied.

Those findings reinforce the need for strong enablement. Seller capability still matters enormously. Poor execution can destroy opportunities that a company should have won.

The CEO, however, now has two different commercial problems to solve. The first is the traditional enablement question: Once we are in an opportunity, can our sellers execute effectively enough to win? The second is an earlier and potentially more strategic question: Did we enter the buying organization soon enough to influence the decision in the first place?

Solving the first without addressing the second can produce a highly capable sales organization that repeatedly arrives after another supplier has helped shape the buyer's thinking. The Forrester 68%/80% finding suggests that disadvantage can be extremely difficult to overcome.

That is why I believe CEOs should subject their 2027 enablement strategy to five tests before approving another year of investment.

Five Questions to Ask Before Approving the 2027 Enablement Budget

1. Where does revenue begin before it becomes pipeline?

Ask the CRO and enablement leader to identify the earliest observable business conditions that suggest a future opportunity may be forming. If the conversation immediately moves to MQLs, website activity, intent scores, leads or pipeline, continue asking questions. Those mechanisms identify when demand becomes visible to the existing commercial infrastructure; they do not necessarily identify when the conditions producing that demand began.

A useful CEO exercise would be to take the company's 20 largest wins from 2026 and work backward. Determine what changed inside each customer's business that eventually created the reason to buy, when that change became externally observable and when the commercial organization recognized it. The gap provides the first meaningful measure of commercial latency.

2. What changed because of our enablement investment?

The CFO and CRO should be able to put three years of enablement investment on the table, including people, training, methodologies, major technology platforms, content infrastructure and AI. Those investments should then be considered alongside commercial outcomes such as win rate, deal value, qualified opportunity creation, sales velocity, executive access, account expansion, competitive displacement and revenue productivity.

Perfect attribution is neither realistic nor necessary. Commercial organizations do not operate that neatly. What should exist, however, is a credible management narrative connecting enablement investment to commercial performance. If the company cannot establish that connection, the immediate response should not necessarily be to reduce the enablement budget. It may be to change the function's accountability.

3. How late are we arriving?

Take 20 significant wins and 20 significant losses and reconstruct the timeline. Determine when the underlying business condition emerged, when it could reasonably have been detected, when the company recognized it, when Sales engaged, when the opportunity entered CRM and, where possible, when the eventual winner established meaningful access to the buying organization.

Those gaps may be uncomfortable, which is precisely why the exercise matters. Commercial latency belongs on the 2027 operating dashboard alongside pipeline coverage, win rate and sales velocity. If competitors consistently establish access before your organization recognizes the opportunity, another sales methodology is unlikely to solve the underlying problem.

4. Are we using AI to change the commercial system or simply make the existing one faster?

CEOs should review the 2027 AI enablement roadmap with a different standard. AI coaching, content generation, prospecting, call analysis and account preparation may all produce useful productivity gains, but the larger question is what the commercial organization can now do that it could not do three years ago.

Material AI investments should increasingly be connected to one of three outcomes: earlier access, greater decision influence or a higher probability of winning. Productivity remains important, but productivity without commercial advantage is ultimately just cheaper activity.

5. Who actually owns buyer readiness?

Most companies can identify who owns seller readiness. Far fewer can clearly identify who owns understanding when the buyer is changing.

The responsibility is often distributed among Marketing, Sales, RevOps, Strategy, Product, Customer Success and Enablement. Cross-functional participation is necessary, but shared participation is not the same as clear accountability. Someone at the executive level needs responsibility for connecting changing business conditions to account prioritization, emerging stakeholders, seller mobilization and ultimately revenue.

Before the 2027 SKO, every CEO should expect someone on the executive team to answer a deceptively difficult question: Where is revenue beginning to form that is not yet visible in our pipeline?

If nobody owns that answer, the organization has identified a much larger problem than sales training.

Enablement May Not Need a Smaller Budget. It May Need a Bigger Job.

The conclusion from this research should not be that sales enablement has failed. The evidence does not support that conclusion. Good coaching, training, methodology, content and technology matter, and the Corporate Visions research demonstrates how costly poor seller execution can be. The more important question is whether seller readiness remains a sufficiently ambitious mandate. I don't believe it does.

The opportunity for enablement is to move upstream: from seller readiness toward commercial readiness, from opportunity execution toward opportunity recognition, from episodic training toward continuous capability development, from content delivery toward decision intelligence, and from measuring enablement activity toward demonstrating commercial outcomes.

That would give enablement a substantially larger role in the enterprise, but it would also create something many corporate functions struggle to maintain: a clear line between the function's work and an outcome the CEO considers strategically important.

The Question I Would Take Into 2027 Planning

Before approving another dollar of enablement technology, training or AI, I would ask the CRO one question: What are we enabling our sellers to do that materially changes our probability of winning?

Faster onboarding, better content, more coaching, increased productivity and stronger methodology adoption are all legitimate answers, but they are no longer sufficient answers. CEOs should also understand whether the company is seeing opportunities earlier, entering buying organizations before preferences harden, gaining executive access sooner, influencing how problems are defined before requirements are established, reducing commercial latency and ultimately winning more often because of those capabilities.

For years, companies have invested in increasingly sophisticated systems for helping sellers win opportunities. Forrester's latest buyer research points toward the next problem CEOs need to solve: 68% of B2B buyers already have a front-runner when their purchasing process begins, and 80% of the time that front-runner wins.

If that research is even directionally representative of your market, it should change the enablement conversation heading into 2027.

The issue may not be that your sellers aren't capable enough. They may not need another methodology, another certification or another AI productivity tool.

They may be extremely well prepared to compete. They may simply be arriving too late. CEO Weekly captured this CEO priority here: https://ceoweekly.com/modernizing-the-revenue-engine-brian-shea-on-aligning-commercial-operating-systems-for-2027/

www.LucrumPartners.co