The Fundamentals of Selling in the AI Age: A Conversation with Steve Richard

I’ve known Steve Richard for years, going back to when we used to see each other regularly on the conference circuit. Now he’s the SVP, Revenue Enablement at Mediafly. When we reconnected recently for the Sales Operator Series interview, I was curious to hear how he thinks about selling in a world that looks very different from when we first met. 

Steve, like everyone, is experimenting with AI. He’s found some impressive applications, particularly around research, meeting prep, messaging, call analysis, and helping sellers navigate internal resources. 

Despite all that, he continues to emphasize how much the fundamentals of selling still matter. Maybe more than ever. 

Here are a few of my favorite takeaways from our conversation. You can also watch the full interview here. 

AI Can Help With the Process, But It Can’t Build the Relationship

Steve pointed out just how much salespeople can now outsource to technology. AI can prepare you for a meeting, analyze a call, recommend next steps, identify the right prospects and even create highly targeted messaging for them. 

All of that is incredibly useful, but Steve noted some great examples of where technology falls short. He’d recently been taking calls from AI vendors, and despite selling some very sophisticated technology, the sales experience itself was terrible. They were asking him basic questions that could (and should) have been answered with a few minutes of research. 

The obvious irony is people selling AI aren’t actually using it to prepare for their sales conversations. It’s a good reminder that more or better sales tools don’t automatically create better selling. 

The sales person still has to take the time to understand the person on the other side of the conversation, establish credibility, ask good questions, and build trust. 

Buyers Don’t Always Know How to Buy

Something many sellers forget is that buyers don’t always know how to buy what you’re selling. A salesperson might have ten or fifteen conversations about a particular type of solution. They know the tool and the category backward and forward. On the other hand, the buyer might make that decision once every few years. 

That creates an enormous experience gap. Even if a prospect leaves a demo thinking, “That was great!,” they may still need to convince a CFO, a manager, IT, procurement, or an executive team. They need to understand who needs to be involved, what those people will care about, and what the organization requires before it will say yes. 

The salesperson’s job is to help the buyer navigate the buying process, internally and externally. That means asking questions like: Who else needs to be involved? How have you made decisions like this before? What does your organization prioritize? What would cause this initiative to get approved (or killed)? 

These conversations help create what Steve called a “collective learning experience,” and give the seller a much better chance of actually getting the deal across the finish line. 

We Need to Get Better at Connecting the Dots

Another theme we kept returning to was the difference between selling features and creating business value. Steve believes sellers need to be able to connect what they’re selling to the outcomes the business actually cares about. It sounds simple, but it’s easy to lose sight of. 

We’ve spent years building increasingly structured, sophisticated sales processes, and sometimes it feels like adhering to the process takes precedence over creating a truly good sales experience. 

The best sellers understand the problem deeply and know how to connect it to the value their solution can create. 

Enablement Doesn’t End When Training Does

Steve also shared an example from Mediafly that really illustrated how difficult behavior change can be (a problem we are intimately familiar with here at Ambition). 

His team knew that building a value hypothesis early in the sales process improved win rates. They made it the center of their playbook—training reps on it, building a KPI around it, and inspecting whether it was happening. 

And still, some reps weren’t doing it. Why? All the tools and training were there. 

Eventually Steve’s team discovered that it wasn’t a knowledge or enablement issue. Rather, some reps just didn’t think the exercise was useful. Just because you teach someone what to do doesn’t mean they’ll believe in it, remember it, or actually do it when the pressure of a deal takes over. 

And that’s exactly why managers are so important! Enablement can introduce a concept and training can teach a skill, but the manager has to reinforce it in the correct context for it to actually work. 

Maybe We Should Go Back to the Classics

We ended the conversation talking about what Steve thinks will really matter in sales over the next year. His answer is basically the opposite of technology. 

It’s the classics. That’s right—books. 

Steve thinks sellers need to go back to the foundational sales methodologies that have been around for years: SPIN Selling, Challenger, Major Account Sales Strategy, and so on. 

He expressed frustration that so many salespeople have never actually learned them. Lots of orgs have gotten wrapped up in teaching sellers how many calls to make, which fields to fill out, and which tools to use, but failed to actually teach them how to sell. 

AI is going to make the best salespeople more productive, helping them research faster, remember more, and prepare more thoroughly. But the ones who will really stand out will be those able to carry on a great conversation. 

Understanding the problem, creating trust, connecting business value, and helping a buyer navigate the decision making process are skills that AI can’t automate. The fundamentals will continue to set great sales experiences apart. 

If you enjoyed this recap, watch the full interview and more Sales Operator Series episodes here.