The #1 Way to Win as a GTM Exec in the Age of AI: Be a True Product Guru. Know Your Space 10x Better Than Any Customer. | Saa Str
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The #1 Way to Win as a GTM Exec in the Age of AI: Be a True Product Guru. Know Your Space 10x Better Than Any Customer.
by Jason Lemkin | Artificial Intelligence (AI), Blog Posts, Saa Str. Ai
It’s not enough to be a “people person” anymore. Not even close.
Here’s a test I want every sales leader to try right now: Upload your company’s pitch deck, product documentation, and competitive battlecards to Claude or Chat GPT. Then ask it hard questions—the kind your best prospects ask. Technical questions. Industry-specific questions. Competitive comparisons.
That AI will outperform 80% of your sales team. Right out of the box.
And here’s what makes it worse: AI with memory gets better with every interaction. It compounds knowledge. It never forgets the Q3 release notes or confuses them with the Q4 roadmap.
Your average sales exec? They plateau at month six and start looking for their next job at month twelve. Many never even really learn the competitive landscape. Many never even use their own product.
So here’s the uncomfortable question every GTM leader needs to answer: If your prospects can get better answers from an AI that has your data than they can from talking to you… why would they talk to you?
The Challenger Sale methodology identified this years ago: the “relationship builder” profile—the classic “people person”—was one of the worst-performing sales archetypes. AI didn’t create this problem. It just accelerated it.
Being able to chat about who won the NBA finals doesn’t close deals. Knowing your product cold does. Understanding your prospect’s specific industry challenges does. Having deployed solutions for similar companies does. Teaching prospects something they didn’t know about their own business does.
I hear it constantly from sales candidates: “I’m a great people person. People like to talk to people.”
But people don’t want to talk to you because you’re a people person. They want to talk to the best solution architect in the world who also deployed their exact use case at their buddy’s company down the street.
Story #1: I had a demo recently for an enterprise AI product. Should have been a slam dunk—great product, real traction, I came in ready to buy.
Then I asked about their MCP support. The rep had no idea what I was talking about. When I mentioned Claude, they said “my guys will look into it.” When I pressed on technical details, they responded: “Your secret to being good at AI was really sick prompts.”
Story #2: One of my Saa Str Fund portfolio companies was meeting with their largest prospect ever—potential $1M deal. The first meeting included their well-regarded CRO, someone with a strong background in “technical selling.”
When the prospect started asking technical questions, the CRO looked confused and asked: “What’s an API call?”
For the follow-up meeting, the founders made a brutal decision: they left the CRO sitting in the lobby and went into the meeting themselves.
We were with an AI leader recently. They closed a seven-figure deal while we were there. The solution architect left the sales team behind. Closed it without them. Didn’t want to talk to the sales team. Sales team didn’t know the product. They added no value.
Story #3: A 3M a Year!! But They Wouldn’t Talk to the New CRO
Instrad, they just worked directly with the head forward delpoyed engineer. They refused to talk to the CRO. The senior FDE was on site, getting the product deployed. The CRO was still learning the industry.
You Cannot Sell Value If You’re Not a Product Expert. Be Honest. Are You a True Guru?
Let me be blunt: most sales folks want to talk with a war sheet, a tear sheet. They know six things. You cannot sell value if you’re not a product expert.
Value-based selling means providing value. You cannot provide value in the age of AI if you do not know the product cold. Ideally, you know how to deploy it, how to get it going, how to deploy real value—not just having a valuation calculator on your website that says 18 months down the road the product will work.
The worst sales rep you can hire today is the one that tells you they’re a “great people person.” Who cares? Your prospect wants someone who can say: “I want your AI SDR deployed in 30 days. I want it to get you this amount of quota. I want to do this workflow. Here’s exactly how we’ll do it.”
The rep who says “Oh, it sounds good, yeah, we can do that”? That’s not going to work.
I really think 70-80% of the sales executives I’ve worked with over the last five or six years don’t know their product cold. If you look back at your top couple sales reps—whatever era, pre-AI, doesn’t matter—the top ones weren’t just good schmoozers. They knew the product cold. I call them “sales magicians,” but they’re not magical. They just know how every nook and cranny works.
Know the product better than an AI trained on your documentation. This is table stakes. If Chat GPT with your docs can answer questions better than you can, you’re already obsolete. You need to know the edge cases, the gotchas, the workarounds, the roadmap context that isn’t in any document.
Know your competitive landscape cold. Not just the talking points on your battlecard. Actually know what your competitors do well, where they’re ahead, where you’re behind. Be honest about it. Sophisticated buyers can smell BS immediately. When you’re honest about gaps, you build trust. When you’re deceptive, you lose the deal—or worse, you win it and create a churn problem.
Know your customers’ industry better than they do. This is the Challenger approach: teach, tailor, take control. You need to walk into a meeting and show your prospect something about their own business they didn’t know. You need pattern recognition across dozens of similar deployments. You need insights they can’t get from Google or Chat GPT.
Know how similar customers deployed and succeeded. “We did exactly this at Company X in your industry” is worth more than any feature demo. Specific use cases, specific outcomes, specific lessons learned. This is knowledge AI can’t have because it requires being in the room for those implementations.
Know what questions to ask that prospects didn’t even know they needed to answer. This is where the magic happens. AI isn’t great at this. The best sales conversations don’t just answer questions—they reframe how the prospect thinks about their problem.
Here’s the hard truth: if a sales exec isn’t curious enough to know the product reasonably well before they start, they never will.
This isn’t a training problem. It’s a hiring problem.
Candidates who haven’t signed up for a trial of your product before the interview? Who can’t articulate your basic value prop in their own words? Who haven’t poked around your competitors’ websites?
That’s not lack of preparation. That’s a fundamental lack of curiosity and initiative that tells you everything you need to know about how they’ll show up for customers.
And it compounds. Leaders who don’t know the product hire teams under them that don’t know the product either. And they will lose to competitors whose sales teams do know it cold.
What AI Actually Does Better Than Most GTM Execs
Let’s be specific about what you’re competing against:
Product knowledge. Upload your docs and AI knows your product better than anyone but your founders and product team. It doesn’t forget. It doesn’t confuse releases. It doesn’t tell prospects about features you deprecated two years ago.
Availability. 24/7. No scheduling. No “let me get back to you on that.” No timezone gymnastics. The AI is there at 11pm when your prospect is doing research.
Consistency. Same quality answer every time. No bad days. No fumbled demos. No “I’m new here, let me ask my SE.”
Memory. Every interaction makes it better. It remembers what the prospect asked last time. It learns what questions get asked. It compounds knowledge.
Competitive intelligence. Feed it your battlecards and it will articulate your differentiation clearly, consistently, and without the emotional bias that makes reps trash-talk competitors in ways that make sophisticated buyers cringe.
If you can’t beat that—if you can’t add something on top of all that—you’re not adding value. You’re adding friction.
There are still things AI can’t do. But they all require deep expertise, not schmooze skills:
Navigate complex organizational politics. Understanding who actually makes decisions, what their real motivations are, how to build consensus across a buying committee. This requires pattern recognition from doing it hundreds of times.
Build genuine trust on career-defining decisions. When a CIO is betting their job on a vendor selection, they want a human they trust. But that trust comes from expertise, not personality. They trust you because you’ve been in their shoes, you know their industry, you’ve seen what works.
Teach customers something new. Reframe how they think about their problem. Show them patterns across their industry. Challenge their assumptions productively. This is the Challenger methodology, and it requires knowing your space 10x better than your prospect.
Adapt in real-time to unexpected objections or opportunities. When a conversation goes sideways, when a competitor does something unexpected, when a prospect reveals a use case you’ve never heard of—that’s where human judgment matters. But only if you have the foundational knowledge to improvise from.
The Practical Takeaway: The Guru Era is Here in AI B2B
If you’re a GTM exec trying to survive and thrive in the age of AI, here’s the bar:
Could a sophisticated prospect upload your product docs to Claude, add your competitor’s docs, and get better answers than they’d get from talking to you?
Do you know your space—product, competitors, industry, deployment patterns—so cold that you can teach prospects something they couldn’t learn from any AI?
Are you curious enough about your product and market that you’re constantly going deeper, even without being asked?
If no, this might not be the right career for you anymore.
We’re just not going to tolerate mediocre GTM execs in the age of AI. If you don’t add massive value in every conversation—value that an AI with all your data and access to all of Chat GPT couldn’t provide—your prospects will buy from somebody else.
Probably from your competitor whose sales team actually knows the product cold.
The people person era is over. The product guru era is here.
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Key Takeaways
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AI VC AI Mentor: Digital Jason + Amelia AI Startup Benchmarking
-
AI Agent Playbook Free e Books
e Book: Hiring a Great VP of Sales e Book: Raising Capital e Book: The First $1m ARR -
University All Posts Podcasts The Top CROs VC Fundraising Top Videos Q&A Best of Saa Str #1 Bestselling Book Search Everything Join the Community
-
Free e Books
e Book: Hiring a Great VP of Sales e Book: Raising Capital e Book: The First $1m ARR -
AI Annual 2026 Events Overview Sponsors
Event Sponsorship Media Sponsorship
