Gartner Says AI Enablement Will Move Deals 40% Faster by 2029. In Cybersecurity, the Enablement Content Is Wrong Before the Quarter Ends.

On April 1, Gartner published a prediction that by 2029, sales organizations with AI-driven enablement functions will achieve 40 percent faster sales stage velocity than the organizations still running traditional enablement. The survey underneath it went to 227 chief sales officers in August and September of 2025.

The headline number is the one that will end up on a slide. The number sitting under it is the one that should worry a cybersecurity sales leader. Those same organizations reported completing an average of four transformations in the previous twelve months.

This piece covers why stage velocity is the right metric for this category specifically, why Gartner's description of traditional enablement is accurate rather than unfair, why cybersecurity content decays faster than anywhere else in software, what in-workflow guidance actually has to do to earn a number like 40 percent, and what we built to do it.

Stage Velocity Is the Metric That Actually Hurts in Cyber

Stage velocity is how long a deal sits in one stage before it moves to the next one. Not win rate, not pipeline coverage, not activity. It measures whether the deal is going anywhere, which makes it the most honest number in a cybersecurity forecast, because cyber deals mostly do not lose to a competitor. They stop moving.

Matt Dixon and Ted McKenna's analysis of more than 2.5 million recorded sales conversations found that between 40 and 60 percent of forecasted B2B deals end in no decision, and that 56 percent of those losses trace back to the buyer's own indecision rather than a preference for the status quo. I went through where lost cybersecurity deals actually go separately. The short version is that the biggest line in the loss column is a deal that never advanced a stage, and almost nobody tracks it as its own category.

That is why Gartner picking stage velocity matters more here than it would in most software categories. A 40 percent improvement in how fast deals move between stages is a direct hit on the largest loss category cybersecurity sales has. It is not a productivity metric dressed up as a revenue one.

A Reactive Support Function Is an Accurate Description of What You Already Bought

Shayne Jackson, VP Analyst in Gartner's Sales Practice, framed the prediction by saying traditional enablement was built as a reactive support function rather than as a system engineered to drive measurable seller performance, and that enablement has to become an AI-driven function that orchestrates seller behavior in real time.

That is worth reading as a description rather than a criticism, because it describes what most enablement teams were actually chartered to do. A content library responds to a request. A quarterly kickoff responds to a launch. A certification responds to a compliance requirement. Every one of those is downstream of something else happening first, and none of them are present at the moment a deal either advances or stalls.

Gartner's follow-on research from the same 227-CSO survey put a number on the alternative. Sales organizations that give sellers AI-enabled next best actions are 2.6 times more likely to achieve commercial growth. A separate survey of 210 sales leaders found the counterweight: AI is already saving sellers close to five hours a week, and 72 percent of sales organizations fail to reinvest that time into higher-value work. Buying AI does not produce the 40 percent. Putting the guidance inside the work does.

Cybersecurity Breaks Static Enablement Faster Than Any Other Category

Every category has an enablement refresh problem. Cyber has a worse one, and the reason is arithmetic. Q1 2026 alone closed 108 cybersecurity acquisitions worth roughly $47 billion, the second-highest quarterly count in the sector's history. Google finished its $32 billion purchase of Wiz in March. Palo Alto Networks closed CyberArk in February. CrowdStrike took SGNL for $740 million.

A battlecard written in January is describing a company that does not exist in April. The competitor a rep is coached to position against is now a module inside a platform the buyer may already be under contract with, the pricing model changed, the integration story changed, and the person who used to own that relationship got reassigned. None of that shows up in a content library until somebody notices and files a request, which is exactly the reactive posture Jackson is describing.

The buyer is working from stale information in the same direction. 6Sense's 2025 research found that 94 percent of B2B buyers now use LLMs somewhere in their buying process and 83 percent define their requirements before they ever speak to a seller, which means the buyer's first answer about your product came from training data that predates the acquisition. So the rep walks into a call where the buyer knows a version of the market that is months old, carrying enablement material that is months old, and the two errors do not cancel out.

Four Transformations in Twelve Months Is Shorter Than One Deal

This is where the sub-headline number from Gartner's survey does its real damage. An enterprise cybersecurity cycle regularly runs 12 to 18 months. The organization selling into it changed four times in the last twelve. Somewhere inside a single deal, the rep working it absorbed a new territory, a new comp plan, a new methodology, or a new leader, and often more than one of those. I wrote about what a leadership change costs the reps underneath it at more length, and the mechanism is the same one here.

Enablement built on a quarterly refresh cadence cannot stay ahead of that. It is not a resourcing failure or a lazy enablement team. A function that updates four times a year is being asked to keep pace with a market that reprices itself monthly and an internal org chart that rewrites itself quarterly, and no amount of headcount fixes a cadence mismatch.

The outcome is visible in the attainment data. RepVue closed 2025 with cybersecurity at 37.9 percent quota attainment, last among every sub-vertical it tracks, against 43.83 percent for the overall cloud software index. Record demand, expanding budgets for most of the decade, and the reps still miss. The enablement layer is not the only reason, but it is the layer that was supposed to close the gap and structurally cannot.

What In-Workflow Guidance Has to Do to Earn the 40 Percent

Gartner's recommendation is to move beyond static content and training and deliver in-workflow, data-driven guidance. That phrase is doing a lot of work, and it is worth being specific about what clears the bar, because a great deal of what will get sold against this prediction over the next three years will not.

It has to be current at the second of the call. Not current as of the last content refresh, or the last CRM sync, or the last time somebody updated the competitive matrix. In a category where a competitor can be acquired between a first call and a second one, guidance that is a quarter old is worse than nothing, because the rep will say it with confidence.

It has to be specific to this buyer. A generic prompt that could apply to any deal in the pipeline is a distraction with better timing. The rep needs the competitor the prospect just named, the weakness worth pressing on with this particular account, and the answer to the technical question that was asked out loud thirty seconds ago, which is a different answer for every deal.

And it has to arrive inside the conversation the rep is already having, not in a tab they have to remember to open. Everyone I talked to at Black Hat already had enough tools, and the complaint I heard most was that the last real-time tool they tried was distracting. That complaint is correct about most of what has shipped. Information arriving faster is not the same thing as help, and a rep who has to stop and read something is no longer listening to the buyer.

Clear those three and the velocity gain is mechanical rather than aspirational. The stage a deal is sitting in advances when the rep answers the thing that was blocking it, and most of what blocks a cybersecurity deal is a question about the buyer's existing stack that the rep could not answer while the buyer was still on the line.

That Is the Product

KillChain Overwatch is real-time competitive intelligence and sales coaching, delivered live in the call, built for cybersecurity AEs. It listens to the conversation as it happens and puts the specific thing the rep needs in front of them at the moment it changes the call, rather than in a summary afterward when the only thing left to do with it is grade the rep.

Concretely, when a prospect names a competitor, the battlecard for that competitor surfaces on its own, with the counter-positioning and the landmine questions worth asking. When a prospect asks a technical question out loud, the answer lands in under a second, cited from the team's own knowledge base, and when the answer is not in there Overwatch says so rather than inventing one. The competitive intelligence behind those cards is rebuilt from public feeds, including SEC filings, NVD and CISA vulnerability disclosures, MITRE evaluations, and G2, so a card reflects what is true this month rather than what a PDF said last quarter. It is scoped to cybersecurity on purpose, because those are the feeds that decide a cyber deal and no horizontal sales platform has a reason to watch them.

It is not a training tool and it is not built to prop up a weak rep. It is an unfair informational advantage in competitive deals, and a force multiplier for strong reps, the ones who already run good discovery and are losing stages because the intel they needed was sitting in a browser tab they could not open mid-sentence.

That is also the honest scope of the claim. Overwatch does not fix a rep who cannot run discovery, and it does not fix an organization where nobody above the rep can define what good discovery looks like, which is a structural problem I have written about separately. It fixes the gap between what a good rep knows and what a good rep can recall, verify, and use in the eleven seconds they have before the buyer moves on.

2029 Is a Deadline, Not a Forecast

The way a prediction like this usually gets read is as a planning horizon. Three years out, budget it for FY28, revisit at the next kickoff. That reading is wrong in a category consolidating this fast, because the 40 percent is not a reward that arrives in 2029. It is a gap that opens continuously between the organizations that put guidance inside the call and the ones that keep publishing content about it, and it will be measurable in a win-loss review long before it is measurable in a Gartner survey.

Your reps are on calls this week, against competitors who were acquired this quarter, in front of buyers who already asked an LLM about you. If you run a cybersecurity sales team, put it on one call and watch what fires the first time a prospect names a competitor. That is the only demo worth sitting through.

FAQ

What did Gartner predict about AI-driven sales enablement?

In a press release dated April 1, 2026, Gartner predicted that by 2029, sales organizations with AI-driven enablement functions will achieve 40 percent faster sales stage velocity than organizations using traditional enablement methods. The prediction draws on a survey of 227 chief sales officers conducted in August and September of 2025, which also found that sales organizations completed an average of four transformations in the prior twelve months, and that organizations collaborating on enablement content across sales, marketing, and service are 2.4 times more likely to achieve strong commercial growth.

What is sales stage velocity, and why does it matter more in cybersecurity?

Sales stage velocity measures how long a deal sits in a given stage before advancing to the next one, rather than whether it eventually closes. It matters disproportionately in cybersecurity because the dominant loss mode in the category is not losing to a competitor, it is a deal that stops moving. Research across more than 2.5 million recorded sales conversations found that 40 to 60 percent of forecasted B2B deals end in no decision, with 56 percent of those losses driven by buyer indecision, which shows up as a stage that never advances rather than a competitive loss.

Why does static sales enablement content decay faster in cybersecurity than in other categories?

Because the underlying market reprices itself faster than a content refresh cycle can keep up with. Q1 2026 alone closed 108 cybersecurity acquisitions worth roughly $47 billion, including Google's $32 billion acquisition of Wiz and Palo Alto Networks closing CyberArk. A competitive battlecard written at the start of a quarter can describe a company that has been absorbed into a platform by the end of it, which changes the pricing model, the integration story, and the account relationship all at once. Enablement functions that refresh quarterly are structurally behind a market that changes monthly.

References

1. Gartner, Inc. Gartner Predicts AI-Driven Sales Enablement Will Deliver 40% Faster Sales Stage Velocity Than Traditional Enablement Methods by 2029 (April 1, 2026). Based on a survey of 227 chief sales officers conducted August through September 2025. Quotes attributed to Shayne Jackson, VP Analyst, Gartner Sales Practice. Gartner
2. Gartner, Inc. Gartner Survey Finds Sales Organizations That Provide AI-Enabled Next Best Actions Are 2.6x More Likely to Achieve Commercial Growth (May 20, 2026). Presented at the Gartner CSO & Sales Leader Conference, based on the same 227-CSO survey fielded August through September 2025. Gartner
3. Gartner, Inc. Gartner Survey Finds AI Saves Sellers Nearly 5 Hours Per Week, Yet 72% of Sales Organizations Fail to Reinvest Time in High-Value Activities (May 19, 2026). Survey of 210 chief sales officers and senior sales leaders conducted January through February 2026. Gartner
4. Matthew Dixon and Ted McKenna. The JOLT Effect: How High Performers Overcome Customer Indecision. Portfolio, 2022. Analysis of more than 2.5 million recorded B2B sales conversations; 40 to 60 percent of forecasted deals end in no decision, 56 percent of those driven by customer indecision.
5. 6sense. 2025 B2B Buyer Experience Report. Finding that 94 percent of B2B buyers use generative AI tools during the buying process and 83 percent define requirements before contacting a seller.
6. RepVue. Cloud Sales Index, Q4 2025. Cybersecurity closed 2025 at 37.9 percent quota attainment, last among tracked sub-verticals, against 43.83 percent for the overall index.

*Written by Jonathan, co-founder of KillChain Sales. Former offensive security operator, now leading go-to-market for an AI competitive intelligence platform built for cybersecurity AEs. If you run a cybersecurity sales team and you want to see what fires on a live call the first time a prospect names a competitor, book a demo or connect on LinkedIn.*