ISG Software Research Analyst Perspectives

The AI Skills That Set Top Sellers Apart

Written by Barika Pace | Sep 15, 2026, 10:00:00 AM

For Chief Revenue Officers, the central question about artificial intelligence (AI) is no longer whether sellers will use it. The question is whether they will use it well enough to improve revenue performance.

Most sales organizations now have access to generative AI (GenAI), embedded copilots, conversation intelligence and predictive insights. Yet access alone does not create an advantage. As AI-generated outreach becomes easier to produce, the market is filling with more content, more activity and more noise. ISG Research asserts that by 2028, one-quarter of enterprises will use GenAI to explain revenue performance drivers, incentive outcomes and forecast variance in natural language, improving leadership confidence and decision-making.

The sellers who stand out will not be those who automate the greatest number of tasks. They will be those who combine AI fluency with judgment, customer understanding and disciplined execution.

For CROs, this creates a new talent mandate. AI capability must become part of the sales operating model, coaching system and definition of seller excellence. Five skills will increasingly separate top performers from the rest.

1. Asking Better Questions

Effective AI use begins with the ability to frame a problem clearly. Sellers who enter vague prompts receive generic outputs. Sellers who provide context, define the audience, specify the commercial objective and establish constraints receive more useful results.

This is more than prompt writing. It is structured thinking. A strong seller can explain what is known about the account, identify what remains uncertain and ask AI to support a specific decision.

Instead of requesting “an email for this prospect,” for example, the seller might ask for three executive outreach approaches based on the company’s stated priorities, recent business changes and the likely concerns of its buying committee.

CROs should treat question quality as a coaching priority. It reveals how well sellers understand the customer and how intentionally they are using technology.

2. Validating AI-Generated Insights

AI can summarize information, identify patterns and suggest next steps, but it can also produce inaccurate, incomplete or weakly supported conclusions. High-performing sellers do not confuse speed with truth.

They verify important account details, challenge assumptions and distinguish between evidence and inference. They also know when an AI-generated statement is not ready to be used in front of a customer. This is especially important in complex sales, where one incorrect claim or superficial recommendation can undermine credibility.

The CRO’s role is to create clear standards for responsible AI use. Sellers need approved data sources, practical guidance on confidentiality and a defined process for reviewing high-impact outputs.

Governance should not slow adoption. It should make AI safe enough to scale.

3. Turning Data into Commercial Judgment

AI can make large volumes of customer, pipeline and activity data easier to interpret. The differentiating skill is deciding what the information means and what action it should trigger.

Top sellers connect signals across the customer journey. They may recognize that declining engagement, a change in executive sponsorship and a delayed technical review collectively indicate deal risk. They can then decide whether to rebuild the business case, engage a new stakeholder or revise the close plan.

This is where AI becomes more than a productivity tool. It becomes a decision-support capability.

CROs should evaluate whether sellers are using AI to improve prioritization, opportunity strategy and forecast quality, not simply to complete administrative work faster. The relevant question is not how much time AI saves, but whether it helps the organization make better revenue decisions.

4. Personalizing with Relevance, Not Volume

GenAI can create personalized messages at scale, but scale without relevance only accelerates poor selling. Buyers can recognize outreach that is technically customized but commercially empty.

The best sellers use AI to prepare more deeply. They connect a prospect’s business priorities to a meaningful hypothesis, tailor questions to the stakeholder’s role and communicate a credible point of view. AI helps them move faster, but the seller remains accountable for the insight.

For CROs, the performance measure should shift from output to impact. Rather than rewarding the number of messages produced, leaders should examine response quality, executive engagement, meeting conversion and progression through the buying process.

The objective is not more personalization. It is more relevance.

5. Collaborating with AI While Preserving Human Trust

Sales remains a human discipline. Customers still expect sellers to listen, interpret nuance, navigate competing interests and demonstrate empathy. AI can support these behaviors, but it cannot replace the trust created through a credible relationship.

Top sellers know which work to delegate and which work to own. They may use AI to prepare for a meeting, summarize a call or identify follow-up actions. During the customer conversation, however, they remain present. They listen for hesitation, adapt their approach and make judgments that require context and emotional intelligence.

CROs should reinforce this balance. The goal is not to remove the seller from the sales process. It is to remove low-value friction so the seller can spend more time creating value with the customer.

Building the AI-Enabled Sales Organization

These five skills will not develop through tool deployment alone. They require enablement, coaching, measurement and leadership example.

CROs should define role-based use cases, incorporate AI into deal reviews and provide sellers with opportunities to practice in real commercial scenarios. Managers must also be equipped to assess the quality of AI-assisted work, not just whether a tool was used.

The competitive divide will not be between sales organizations that have AI and those that do not. It will be between organizations that use AI to generate activity and those that use it to improve decisions, customer relevance and revenue outcomes.

For CROs, that distinction should shape the next generation of sales talent strategy. The strongest sellers will not compete with AI. They will know how to direct it, challenge it and apply it while preserving the judgment and trust that customers value most.

Regards,

Barika Pace