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Enablement Leaders in 2026: Engineering Growth From the Base With AI

Ray Makela
Ray Makela
February 17, 2026
8 mins
Beyond Spreadsheets: The Discipline of Commercial Due Diligence

When we brought together enablement leaders for SBI’s Q1 2026 Enablement Growth Forum, a familiar pattern showed up with a new level of urgency.

Churn is up. Sales cycles are sticky. Win rates are under pressure. And almost every CEO we talk to is asking a version of the same question: “How do we grow from the base, protect NRR, and actually get value from all the AI we’ve bought?”

In this session, Rick Karlton, who leads SBI’s advisory and talent practice, and Craig Riley, who leads SBI’s research team, and I focused on that intersection: what SBI’s latest research is telling us about outperformers, and what it means for enablement leaders who are staring down 2026 targets.



Why enablement feels heavier going into 2026   

 

Craig opened the session by sharing data from SBI’s CEO Growth Sentiment Index. On the surface, the news is good: overall CEO sentiment going into 2026 is the highest we’ve measured in two years.

Underneath that optimism, three concerns dominate:

  • External market shocks. Many CEOs felt blindsided by events in 2025 and expect more turbulence this year.
  • Differentiation under pressure. It’s getting harder to stand out as buyers see more “good enough” alternatives.
  • Execution gaps. Even when products improve, renewal and expansion often lag.
  • Customer churn
  • Elongating sales cycles
  • Win rate declines

On the metrics side, the same three red lights kept coming up:

As a result, one priority rose to the top for both the overall market and the outperformers in our study: Realigning commercial resources to grow revenue from the base.

For enablement leaders, that changes the brief. It’s no longer enough to run strong programs and a successful SKO. You’re being asked to engineer growth from the base — and to prove it.

What outperformers are doing differently


To understand what “good” looks like, Craig segmented our research into two groups: companies that exceeded their 2025 goals (“outperformers”) and everyone else. 

 

Three differences matter for enablement. 

 

1. Treating renewal and expansion as a redesign problem 


When we asked CEOs which GTM processes they expect to overhaul in 2026, one gap jumped out. 

  • Only 18% of all CEOs said they plan a major redesign of renewal and expansion.

  • 41% of outperformers said the same — a statistically significant difference. 

Outperformers are not assuming “more of the same, but better” will fix NRR. They are: 

  • Rebuilding what renewal and expansion should look like in a world of bigger buying groups, higher scrutiny, and AI-enabled insights. 

  • Examining friction in handoffs, data, and ownership across Sales, Customer Success, and Marketing. 

  • Updating account guidance, not just issuing generic “grow from the base” mandates. In our data, 48% of outperformers — vs. 36% of others — are adjusting guidance on which accounts to prioritize for growth. 

For enablement, that means your playbooks, certifications, and coaching rhythms have to line up with new renewal and expansion motions, not legacy ones. 

 

2. Shifting investment toward GTM capacity and AI readiness 

 

The second difference is how outperformers think about capital and talentOn the headcount side, outperformers are more likely to: 

  • Increase quota-carrying capacity, especially in large and key accounts. 

  • Re-evaluate frontline manager spans of control and middle-management layers. 

  • Keep revenue enablement roughly stable overall, with a slight tilt toward growth (29% planning to increase vs. 17% to decrease). 

On the capability side, we saw a subtle but important shift: 

  • Across the full sample, CEOs talk about “upskilling sellers and managers” in broad terms. 

  • Outperformers are moving budget from generic training toward AI-specific readiness — helping teams use AI in core GTM workflows, not just for one-off tasks. 

As Craig put it in the session, many outperformers believe they already have the right core skills; the question is how to scale those skills and make them AI-native, rather than starting from scratch. 

 

3. Using AI to decide “what’s next,” not just “what happened”

 

We also asked where CEOs are deploying AI across a set of use cases. Most organizations are still focused on automation

  • Email personalization 

  • Content creation 

  • Call summaries and CRM updates 

Those use cases matter, but we consistently see a ROI gap when the time saved isn’t redeployed into higher-value work. Outperformers are more likely to invest AI capacity in analytics and prediction, particularly in: 

  • Pipeline prediction and forecasting 

  • Competitive intelligence 

  • Customer churn prediction, where the gap between outperformers and the rest of the market is especially large 

In other words, they’re using AI to answer “where should we focus next?” rather than just “what happened?” For enablement, that changes the AI conversation from “Which tool do we roll out?” to “How do we help managers and reps work differently when these signals show up?” 

 

What we heard from enablement leaders 


The research is only half the story. The most valuable part of the Forum was hearing how enablement leaders are trying to close the gap between strategy and field execution. Three themes came up repeatedly. 

1. SKO as episode one, not the entire season 

Many teams are just coming off SKO, and the frustration is familiar: big investment, strong energy, and then a slow fade by mid-year. Leaders who are seeing better traction are reframing SKO as the kickoff to a 12‑month enablement arc, not a standalone event. We heard examples of: 

  • Quarterly “growth days” tied to specific initiatives (for example, new product launches), often co-led with Product Marketing, to keep SKO themes alive and relevant throughout the year.

  • A clear view at SKO of “what the rest of the year will look like”—so sellers know there will be follow-up sessions, certifications, and manager-led reinforcements, not just a one-and-done event.

That approach also makes it much easier to tie SKO themes to the NRR and growth-from-the-base agenda we discussed earlier.

2. Bringing the customer into the room 

Several leaders shared that the highest-rated sessions at their recent kickoffs were live customer panels and interactions. One enablement team invited clients to talk candidly about:

  • Why they chose the vendor

  • What keeps them staying

  • Where they still see friction or missed opportunities

The feedback was both validating and uncomfortable — and that was the point. In many cases, customers reinforced messages enablement has been delivering for years, but with added weight. For enablement, this is a practical reminder: if you want to change seller behavior around renewals and expansion, it helps to let customers describe, in their own words, what great looks like

3. Measuring impact through competencies and telemetry 

We also spent time on the measurement question: how do you show that enablement is moving the needle on the metrics CEOs care about?

Two practices stood out:

  • Competency-based assessment. Rick shared examples of organizations “snapping the chalk line” early in the year with structured assessments for sellers, CSMs, and managers — then revisiting those scores 6–12 months later to see where SKO themes and ongoing programs are actually changing behavior.

  • Linking behavior to performance data. Some teams are using AI to score discovery calls or account plans against a rubric, then correlating those scores with win rates and deal size. That lets them say, with confidence, “When we see this behavior, we see this lift.”

Neither approach is simple, but both are far more compelling than a post-event satisfaction survey. 

 

Engineering NRR with usage cohorts 

 

The last part of our Forum shifted from SKO to NRR mechanics, drawing on SBI’s Engineering SaaS Account Growth research.

Working with QuadSci, we analyzed:

  • Over 180 billion telemetry data points
  • 9,100 commercial outcomes (renew, churn, expand)
  • 15,000+ survey data points across 244 decisions

Two findings are especially important for enablement.

Usage drives renewal — but volatility hides the signal

First, the obvious but underused insight:

  • Solution usage explains roughly 80% of a customer’s renewal decision — more than any other factor we tested (firmographics, historical performance, post-sales interventions, and so on).

If you know usage, you can usually predict renewal and growth.

The problem is volatility. Usage doesn’t follow a neat, steady line. Accounts bounce above and below a “renewal threshold” multiple times over the relationship, for reasons ranging from new leadership to shifting priorities.

That volatility creates two execution traps:

  • Teams can’t reliably distinguish unsalvageable accounts from those that are truly at risk but saveable.
  • They keep running renewal motions on healthy, growth-ready accounts, missing expansion opportunities.

In many organizations, CSMs are even told to run the same renewal playbook across their entire book of business, regardless of usage pattern.

Cohorts give you a new lens

To cut through that noise, Craig’s team built a composite view of each account using two signals:

  • Usage level – how much, how broadly, and how deeply the solution is being used
  • Usage consistency – how predictable the pattern is over time (not how “flat” it is)

When you plot those two dimensions for thousands of accounts, something interesting happens: natural clusters — or cohorts — emerge, each with a distinct usage pattern and highly consistent commercial outcomes.

Across companies, we repeatedly see six cohorts:

  • Explorers – new customers with emerging usage patterns
  • Converts – usage and consistency have crossed the renewal threshold
  • Enthusiastic adopters – fast-growing, varied usage; still settling into a pattern
  • Power users – high, consistent usage; your healthiest growth accounts
  • Strugglers – low, unstable usage; value and usage are not yet linked
  • Disconnected – very low usage; often shelfware or intentional churn

Knowing a customer’s cohort lets you:

  • Predict renewal and growth with roughly 90% accuracy, up to 12 months in advance
  • Target interventions where they’re most likely to change the outcome
  • Avoid overserving accounts that will renew anyway, while underserving accounts that are primed for expansion
  • Align playbooks, competencies, and manager coaching with where the account actually is, not where we assume it is

From an enablement perspective, cohorts create a much sharper brief:

  • What does good discovery look like in a Struggler account vs. a Power User account?
  • How should a CSM’s skills differ when working Explorers vs. Disconnected accounts?
  • Which competencies matter most in the part of the lifecycle where we’re losing NRR today?

Those are the kinds of questions that connect your work directly to the CEO’s growth-from-the-base agenda.

Overcoming adoption barriers

 

If there’s a throughline in what we heard at the Q1 Forum, it’s this:

  • The old playbook of content-heavy SKOs, generic coaching, and one-size-fits-all renewals won’t carry 2026.
  • Outperformers are already rebuilding renewal and expansion, investing in AI and GTM capacity, and using data to decide where to focus.

That’s both a challenge and an opportunity.

The challenge is that enablement teams are already stretched, often responsible for everything from onboarding to analytics. The opportunity is that few functions are better positioned to connect strategy, skills, and systems than enablement.

As you look ahead to the rest of 2026, the questions I’d encourage you to ask are:

  • Enablement is increasingly expected to sit in the middle of that system, not on the edges.
  • How do our SKO themes show up in QBRs, account plans, and coaching conversations?
  • Where can we use AI and telemetry to tighten the connection between enablement and NRR?
  • And what would it look like for our team to be seen not just as content owners, but as true growth engineers for the base?

Those are the conversations we’ll keep having in this Forum — and the ones that will define enablement’s impact in the year ahead.

 

 

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