AI Can Power the Sale—But Human Sellers Still Win the Moments That Matter

Artificial intelligence is rapidly changing how B2B sales organizations operate. From account targeting to outreach optimization, AI is helping sellers work faster and more efficiently than ever before.

But efficiency doesn’t win complex deals.

In the video below, John Elsey, CEO of Richardson and steward of the Challenger methodology, shares a critical perspective on the future of selling: while AI can help sellers earn more customer time, it’s what happens during those moments of live interaction that ultimately determines who wins.

Drawing on decades of experience working with global B2B sales organizations, Elsey explains why the most important moments in the buying journey still belong to human sellers—and how leaders should think differently about where AI fits.

Where AI Earns Sellers the Right to Engage

When applied thoughtfully, AI can dramatically improve how sellers operate before they ever speak to a customer. It can help teams:

• Identify which accounts are most likely to buy
• Prioritize outreach based on intent and readiness
• Develop more effective engagement strategies
• Increase conversion rates and create more selling opportunities

AI excels at analyzing patterns and removing friction from the sales process. In doing so, it helps sellers get into more conversations—and ideally, better ones.

But that’s only the first step.

The 17% of the Buying Journey That Changes Everything

As Elsey notes in the video, only about 17% of the B2B buying journey involves live interaction between buyers and sellers.

That statistic should fundamentally change how sales organizations think about selling.

If sellers only have a narrow window to influence buyers, then those interactions are not interchangeable. They are the moments where differentiation either happens—or doesn’t.

And no amount of automation can compensate for poor performance in those moments.

Why Human Sellers Still Create an Advantage

When buyers engage with sellers, they aren’t looking for information they can find on their own. They’re looking for clarity in the face of complexity.

This is where the human seller still holds the advantage:

• Challenging customer assumptions and status quo thinking
• Reframing priorities and highlighting unseen risks
• Helping buyers navigate indecision and internal disagreement
• Bringing insight that reshapes how buyers think about their problem

AI can inform these conversations. But it cannot lead them.

Challenger Selling in an AI-Enabled World

Elsey’s perspective aligns directly with the core principles of the Challenger methodology. In complex deals, the sellers who win aren’t the most responsive or agreeable—they’re the ones who bring a strong point of view.

AI makes that easier by:

• Surfacing insight sellers can use to challenge more effectively
• Freeing time for deeper preparation and customer engagement
• Helping sellers focus their energy on the deals that matter most

But the act of challenging—teaching buyers something new, reframing their thinking, and guiding them through complexity—remains a uniquely human skill.

The Future Belongs to Sellers Who Can Challenge

The future of B2B sales isn’t about replacing sellers with technology. It’s about using AI to elevate the impact of human sellers in the moments that matter most.

As Elsey makes clear, organizations that win will be those that combine AI-enabled efficiency with Challenger-led insight—using technology to support sellers, not substitute for them.

That’s how sellers move beyond participation and become indispensable to the buying decision.