What Still Matters in Sales When Everyone Has AI

AI is supposed to make us faster. But in a lot of go-to-market organizations, I'm not sure that's what’s actually happening.

We have more data, more automation, more AI tools, more ways to generate content and more systems designed to help sellers move faster. At the same time, it can feel like everyone is moving through more noise, producing more words and struggling to get to the things that actually matter.

That tension came up repeatedly in my conversation with Sam Jacobs, founder and CEO of Pavilion, on the Sales Operator Series.

Sam has been in go-to-market for more than two decades, including time as a CRO and now as the founder of one of the largest communities for revenue leaders. His view is that we're in the middle of a genuine changing of the guard. The fundamentals of selling haven't disappeared, but the environment around them has changed dramatically.

And that may make the human parts of selling more valuable than ever.

I'm going to give a recap of our conversation here, and you can check out the full episode below.

AI gave us more output, but not necessarily more productivity

One of the ideas Sam and I kept coming back to was the gap between what AI promised and what organizations are actually experiencing.

The expectation was that AI would save us time, but instead, many people are just producing more.

Sam described it as a “tsunami of words.” It's incredibly easy to take an idea, throw it into an AI model, iterate on it repeatedly, generate a presentation or document and send the whole thing to someone else.

The problem is that the thinking hasn't necessarily been completed.

I can take seven minutes of voice notes, drop them into an AI tool and get something that looks polished in seconds. But that doesn't mean I've thought through how the person receiving it will react, whether the argument makes sense or whether I've actually arrived at the right conclusion.

Sam described a similar phenomenon happening inside organizations: people are doing half the thinking, letting AI do the other half, and then handing the output to someone else to figure out.

Is that productivity, or is it just moving half-baked work downstream more quickly? 

It also creates a strange version of “good cop, bad cop” in which AI becomes the bad cop. My AI wrote it. I didn't say that.

Sam's point is this: If you send something, it's on you. Whether you created it yourself or AI created it for you, you own the output.

We may have gotten worse at being present

This is where the conversation moved from AI into something much more fundamental about selling.

I asked Sam about a thesis I've been thinking about: that sellers haven't necessarily gotten worse at generating activity or following process, but that we've gotten worse at some of the human parts of selling—listening, qualification, alignment and getting someone to genuinely buy into an idea.

Sam agreed, although he put a sharper point on it.

He says he doesn't think salespeople today are necessarily more talented than they were in the past. In some ways, he thinks they're actually less capable of critical thinking and being present.

We've spent years turning sales into an assembly line. A lead enters the system. A seller follows the sequence. A qualification framework tells them what to ask. The CRM tells them what stage comes next.

There's obvious value in having systems. But if the system becomes the conversation, sellers can end up “painting by numbers” instead of actually listening to the person sitting across from them.

Sam isn't convinced that putting AI prompts in a seller's ear during a call solves that problem, either. If I'm trying to listen to you while simultaneously reading instructions about what I should say next, I'm not sure I'm actually listening to you at all.

Competition may matter more than salesmanship

One of Sam's more interesting challenges to my thinking was around quota attainment.

It's easy to look at low attainment and conclude that sales organizations have become worse at selling. Sam sees something else happening: competition has exploded.

There are simply more products competing for the same buyers.

In some AI-native companies, sellers are benefiting from enormous demand for compute and AI infrastructure. Sam called this being in the “token flow.” Meanwhile, many legacy SaaS sellers are still fighting for every deal.

The result is that some sellers are operating in incredibly high-demand markets while others are selling into categories crowded with dozens of increasingly similar alternatives.

In that environment, even great salesmanship has limits.

Getting on a plane, meeting someone in person and building a relationship can still work. But it is expensive. And when the underlying products are increasingly commoditized, the sales motion itself has to work harder to create differentiation.

Your personal brand might become part of the product

This was probably my favorite part of the conversation. If I'm reading something on LinkedIn today, I increasingly assume it was generated or heavily assisted by AI unless there's something distinctly human about it.

That changes the value of having a genuine point of view.

Sam and I talked about the idea that, in a world where products become more similar and digital communication becomes more automated, the individual seller may have to become their own brand.

Not “personal brand” in the influencer sense, but something much simpler: Do I recognize your perspective? Do I trust you? Do I actually like talking to you?

If two products are roughly equivalent, that human connection can become a meaningful differentiator.

The challenge is that it's difficult to manufacture at scale. You can't simply hire a hundred people and expect all of them to become exceptional relationship builders with distinctive voices. That's part of what makes genuine human connection valuable in the first place.

The future may be more human, not less

When I asked Sam where GTM will be a year from now, he was appropriately skeptical of making precise predictions.

But one thing he felt confident about was that organizations capable of creating meaningful, authentic experiences will become increasingly valuable.

At the same time, the baseline expectation for software will continue to rise. AI will become table stakes. Products will be expected to understand context, respond intelligently and increasingly do the work users once had to do themselves.

That combination creates an interesting future for sales in which the technology gets better, the products get smarter, and the amount of digital noise continues to increase.

And the things that are genuinely hard to automate—judgment, trust, attention, perspective and qualified human connection—become more important.

It's not an argument against AI, but rather a recognition of theopportunity to use AI to eliminate the work that doesn't require a human so that we can spend more time doing the work that does.

For sellers, that might mean less time generating another email and more time figuring out what a buyer actually needs. Less time following a script and more time listening. Less generic content and more genuine perspective.

Sam's advice for the next phase of GTM was refreshingly straightforward: stay close to the customer and solve their problems.

Listen to the full conversation with Sam Jacobs on the Sales Operator Series to hear our conversation about AI, quota attainment, the changing GTM landscape and why authentic human connection may be one of the most valuable differentiators left in sales.

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