Cracking the Code: Selling AI When No One Knows How to Buy It

AI is the most urgent – and misunderstood – purchase facing B2B buyers today.

Buyers are under pressure to act fast, but uncertainty clouds their decisions. To win in the AI era, sellers must stop pitching features and start teaching buyers how to buy. Why? Because in this moment, confidence, not code, is what closes. Sales leaders need to prepare their teams to meet this challenge.

The Fog of Selling AI

The pressure to sell AI is relentless. Sales leaders report that, despite a flurry of early-stage interest, their sellers struggle to close even when they have a market-leading reputation or a strong product.

Often, when sellers face inertia in the marketplace, they default to the old ways of selling. They may lead with technical jargon, thinking they can wow buyers with concepts they may not understand but that sound impressive. They emphasize product features and benefits, detailing functionality or emphasizing adaptability or speed to implementation.

What many sales leaders don’t realize is that the barrier to selling AI isn’t technical capability or product quality; it’s buyer disorientation. Sellers can tout glossy features and use cases, but buyers are lost in the ambiguity of what AI means to their business.

This surface-level, jargon-laden approach can leave buyers feeling even more uncertain and wondering what they should buy at all – increasing anxiety and stalling deal progress.

That leaves sales leaders with missed forecasts and unmet sales goals. Growth halts and the market sees a company that can’t sell innovation. Once that reputation sets in, it’s nearly impossible to recover.

Appetite Versus Aptitude

The problem is not a lack of buyer interest. McKinsey reported that nearly 80% of large enterprises with at least $500 million in revenue use AI in at least one business function; however, usage is not the same as thoughtful execution. While AI interest continues to soar, AI strategy has not, according to the same McKinsey study:

• Only 28% of large enterprises have effectively embedded AI solutions into business processes
• 25% have a clearly defined road map to drive generative AI (Gen AI) adoption, and 24% have a mechanism to incorporate feedback on Gen AI solutions and improve them over time
• 19% established a compelling change story around the need for Gen AI adoption
• 18% track well-defined KPIs for Gen AI solutions

Buyers feel compelled to invest in AI without understanding how to use it. This gap in understanding and strategy makes buying AI solutions feel risky. When sales teams don’t help buyers understand how AI fits into their overall business strategy, they perpetuate that feeling.

Building a Sales Team for the AI Moment

One mistake that sellers often make is to lead with what they sell, not how they sell. For a disruptive technology like AI, that’s especially true.

But sales leaders can take a different approach. It begins by shifting sellers’ mindset away from the AI product and to the AI buyer.

Sellers who will be successful in selling AI will draw on consultative skills to deeply understand a buyer’s needs and fears before talking about what a product can help achieve. They

• Prioritize open dialogue to build trust, focusing on a buyer’s logical and emotional drivers to help them realize their goals
• Act as a guide, using commercial teaching to illustrate something the buyer may not know about the process to procure AI
• Help buyers realize that their status quo – in this case, hesitating to invest in AI – comes with costs they can’t afford
• Use constructive tension to move the customer from indecision to confidence in making a change

As sales leaders consider how to break through buyer uncertainty, they need sellers to:

• Teach for differentiation: In a saturated market, buyers consider brand reputation, product quality, and customer service to be table stakes. A rep who educates buyers on potential outcomes, alternatives and risks, and stakeholder management – and who provides ongoing insight – will outperform one who shows up with a nice set of slides and a slick AI talk track. Your sellers need to leave a buyer thinking, “I would have paid for that conversation alone.”
• Understand buyer needs: Buyers need to identify the problems they have to solve, not the technology they need to solve them. Sellers should ask thought-provoking questions to understand the buyer’s current state to help prospects articulate their problems and consider problems they aren’t yet aware of but should be.
• Control the sale process: AI deals stall because buyers often don’t have a well-defined process to evaluate and buy. Sellers can relieve that pressure by offering a roadmap that outlines evaluation stages and establishes clear criteria – identifying stops on the journey that the buyer may not anticipate.
• Define outcomes and success metrics: Understanding what success will look like for the buyer clarifies organizational goals and aspirations and reveals what’s at stake for the prospect personally. By understanding what a prospect wants to do, a seller can then translate vague AI ambitions into measurable goals, like decision speed or higher margins. This turns the murky nature of buying AI into a concrete business initiative.
• Use constructive tension: Constructive tension isn’t creating tension between the buyer and the seller; it builds tension between the buyer and their status quo. By using it effectively, a seller can quantify the true cost of standing still, driving buyers to understand why the status quo can’t continue. And because sellers used their consultative skills to build trust, this empowers them to engage buyers in seeing what’s truly at stake

High-performing sales teams don’t simply “sell AI.” They teach buyers how to buy before showing them what to buy. They position themselves not as vendors but as navigators who can guide their clients and prospects to clarity. This clarity reduces risk, builds confidence, and accelerates decisions.

Selling AI is a fundamentally different motion. Buyers navigate a landscape they truly don’t understand, and it is a seller’s job to teach them how it works.

Sales teams that guide buyers’ thinking (rather than their choices) will own the market. Everyone else will watch from the sidelines.

John Elsey is CEO and President of Richardson.