Workforce & Talent

AI Is Widening the Gap Between Top Sellers and Everyone Else

New research from Stripe and Checkr finds AI hands its biggest gains to reps who were already ahead. The deciding factor is not tenure or talent but how well each rep knows how to use the tools.

October 9, 2026 · Workforce & Talent
Laptop showing a business analytics dashboard with bar charts and scatter plots on a desk beside a pencil holder in an empty office

Key Takeaways

  • After AI adoption, managers assigned higher-value tasks to 44% of top-quartile sales reps but only 12% of bottom-quartile reps, in a survey of 236 sales professionals at Stripe and Checkr.
  • Each one-point rise in self-rated AI literacy on a five-point scale was associated with a 0.71-point increase in the benefits reps reported from AI.
  • Salesforce finds top-performing sales teams are 1.7 times more likely than underperformers to use prospecting agents, and the average seller spends only 40% of their time selling.
  • Among sales leaders using AI, 51% say disconnected systems are slowing their AI initiatives, according to Salesforce’s survey of 4,050 sales professionals.

The promise of AI in sales has always been a leveling one. Give every rep the same research assistant, the same email drafter, the same call summaries, and the middle of the team should start to look more like the top. New research suggests the opposite is happening. The tools are reaching everyone, but the gains are pooling with the people who were already winning.

That finding comes from a study reported by Inside AI on October 8, built on interviews with eight C-level revenue executives from the Bain Capital Ventures CRO Advisory Board, a survey of 236 sales professionals at Stripe and Checkr, and more than a dozen advisor meetings. After AI adoption, managers assigned higher-value tasks to 44% of top-quartile reps, compared with 12% of bottom-quartile reps. Managers were also 16 percentage points more likely to report quality improvements for their top performers. For anyone running a revenue organization, that is not a technology result. It is a workforce result.

The Deciding Variable Is AI Literacy, Not Talent

It would be easy to read the gap as proof that strong reps are simply strong at everything. The study points somewhere more useful. Higher performers did report bigger time savings, but the factor most closely tied to benefit was AI literacy. Each one-point increase in self-rated AI literacy on a one-to-five scale was associated with a 0.71-point average increase in reported benefits. That is a correlation from self-reported data, not proof of cause, but it shifts the question from who the company hired to what the company taught.

The executives interviewed described the same pattern in practice. Checkr COO Lindsey Scrase credited creative, account-specific use of AI with separating the best reps from the rest, citing one rep who built a negotiation copilot before such tools were widely available. Accenture’s Kevan Yalowitz made the complementary point: top players can teach themselves a fast-changing toolset, while others need structured training and support to get there. Left to self-service, adoption becomes another advantage that compounds for people who already had one.

The pattern holds at much larger scale. Salesforce’s 2026 State of Sales survey of 4,050 sales professionals across 22 countries found that top-performing teams are 1.7 times more likely than underperformers to use prospecting agents. The same survey found that the average seller spends just 40% of their time selling, and that 46% of Gen Z reps rarely get feedback on their sales conversations while 47% say they lack enough roleplay before customer calls. The reps who most need structured help are the ones least likely to be getting it.

The Data Layer Decides What AI Can Do

The second driver is less personal and more operational. Vercel COO Jeanne Grosser told the researchers that strong agent performance depends on a well-structured data layer that encodes company-specific definitions. An AI tool that cannot tell which accounts count as strategic, or what stage a deal is really in, produces generic output, and only a skilled rep knows how to correct it.

Salesforce’s numbers show how common that problem is. Among sales leaders using AI, 51% say disconnected systems are slowing their AI initiatives. Some 79% of high performers prioritize data hygiene, compared with 54% of underperformers. In other words, the teams pulling ahead are not only better at prompting. They are feeding their tools cleaner inputs, which makes every rep’s output more trustworthy and narrows the room for individual guesswork.

Buyers Are Raising the Bar at the Same Time

All of this is happening while buyers become harder to reach. G2’s 2026 Buyer Behavior Report, based on a survey of more than 1,000 B2B software buyers, found that 82% sourced recommendations from an AI chatbot in the last 24 months, and that by the time a seller gets a call or demo request, the shortlist is often already formed. Evaluation is now the longest buying stage, finance involvement in software decisions rose from 31% to 46% in a year, and nearly half of buyers said their CFO vetoed an approved deal in the last year.

That environment punishes uneven performance. When buyers arrive late, informed, and backed by a skeptical finance team, a team cannot afford a long tail of reps who walk into the room with generic research and an improvised deck. Every conversation has to carry proof, and the gap between the top quartile and the bottom shows up directly in win rates.

The Leveling Playbook

AI will not flatten a sales team on its own. Left alone, it rewards the people with the curiosity, data, and manager attention to exploit it, and it lets everyone else fall further behind. The organizations that close the gap will be the ones that treat enablement, data, and role design as part of the AI rollout rather than an afterthought.

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