Enterprise sellers usually look for the break point in the wrong place. They review the demo. They rewrite the follow-up. They blame procurement.
But the loss often happened earlier.
In a July 16, 2026 post, Tomasz Karwatka reviewed six months of Open Mercato enterprise conversations and concluded that every lost deal was lost in the first two meetings. His line was blunt, and useful, the pipeline does not die loudly, it keeps scheduling meetings, like a book club about your product. Read his original analysis here, Enterprise Deals. Every One We Lost, We Lost in the First Two Meetings.
That diagnosis matters. But the practical implication matters more.
If the deal is effectively decided in meeting one, then meeting one is not where the judgment is formed. It is where the buyer confirms what they already believe. For an early-stage company with no brand, that belief is built before the call, from what the buyer can find, infer, or ask an AI system about you.
The finding
Karwatka’s post is worth reading because it is not theory. It is a post-mortem on real enterprise conversations, over six months, with a clear pattern across the losses. He also explains the emotional trap, enterprise deals never tell you they are dead, they just keep booking time.
That is the right level of pain to name. The false signal is not silence, it is activity. Calendar movement can hide the fact that the buyer has already downgraded you.
Most sales advice responds to that with in-meeting tactics, sharper discovery questions, tighter objection handling, better multi-threading, cleaner next steps. Those are not wrong. They are just downstream.
If the buyer has already decided you do not understand their world, no amount of meeting-two polish repairs meeting-one skepticism.
Wrong place
The broader genre of founder-led sales advice tends to assume the meeting is the battlefield. That is understandable. It is visible, measurable, and emotionally immediate.
But in early-stage B2B, the meeting usually starts with an information asymmetry. The buyer has already done a scan, even if a shallow one. They have looked you up. They may have asked peers. Increasingly, they ask an AI system. They come into the call with a pre-read, whether you wrote one or not.
So the real question is not, how do we run a better first meeting?
It is, what did the buyer read before they joined it?
- Nothing, which means they arrive with uncertainty and low conviction.
- A generic landing page, which signals category-level marketing, not problem-level understanding.
- Published work, which can do something much more powerful, it can show that you already understand their failure mode.
That third option changes the frame. The meeting is no longer an evaluation of whether you get it. It becomes a conversation about whether your approach is right for their context.
What buyers do
For technical founders, this is usually the blind spot. They assume the call is the first real moment of persuasion. It is not.
Before the meeting, a serious buyer is asking basic questions:
- What does this company actually know?
- Have they seen my problem before?
- Do they understand my environment, my constraints, my risk?
- Are they speaking our language, or just selling a tool?
If the answer to those questions is hidden, the buyer fills in the gaps themselves. Early-stage vendors rarely win that exercise. The default fill-in is caution.
That caution shows up in the room as polite interest. The call is pleasant. The notes are positive. The next step is soft. Then the deal cools.
This is why founders over-attribute losses to pricing, or procurement, or timing. Those may be the final explanations. They are not always the cause.
The cause is often that the buyer never reached a point of internal conviction.
Pre-meeting asset
The fix is not a prettier deck. It is not a case study PDF with stock photos and one vague logo line. It is published work that helps a buyer orient before they ever meet you.
That work should do one thing well, demonstrate that you understand the exact problem they live with.
That can take several forms:
- A teardown of a common operational failure in their market.
- A benchmark that shows where strong teams behave differently.
- A written point of view on the tradeoff they are already debating internally.
What matters is specificity. The piece should sound like it was written by someone who has sat with the problem, not someone trying to generalize it.
This is the mechanism. Good published work reduces the meeting’s cognitive load. It moves the call from, “What do you even do?” to, “How would this apply to us?”
That shift matters because evaluation is slower than conversation. Conversation is better than interrogation. And a buyer who is already oriented is easier to advance.
Useful public work does the persuading before anyone joins the video call.
Two-week test
You do not need a marketing team to test this.
Take your last ten lost deals. For each one, ask a simple question, what could the buyer have read about us before the meeting?
- Write down the answer for each deal.
- Mark whether the answer was nothing, a generic page, or a useful published piece.
- Look for the pattern.
If most of the answers are nothing, you have found a likely failure mode.
That does not prove content alone would have saved every deal. It does tell you the buyer had little to work with before the first call. In enterprise sales, that is rarely neutral.
Founders like tests because they turn a vague complaint into a visible problem. This one does that quickly. It also keeps you honest. If your content is thin, or too broad, or too product-centric, the exercise will show it.
What to publish
Three artifacts are enough to start.
Problem teardown
Describe the failure mode your buyer already recognizes, but not in their internal language. Write it as a diagnosis. What breaks, why it breaks, what teams miss, and what the cost looks like.
This gives the buyer something familiar, but sharper than their own shorthand.
Decision benchmark
Show the range of approaches in the market, and the tradeoffs between them. Keep it honest. The goal is not to sell your answer as magic. The goal is to help a buyer see the decision structure clearly.
That is especially useful for first-time sellers, because it signals maturity without posturing.
Point of view
Publish a clear position on the issue buyers are already arguing about internally. For example, why a certain workflow breaks at scale, why a common integration creates risk, or why a team’s current metric hides the real problem.
Strong point of view is not contrarian for its own sake. It is useful because it helps a buyer tell whether you have an opinion shaped by experience.
Each artifact changes the first meeting in a different way. Together, they do more than support demand generation. They create pre-meeting trust.
Where it ends
There is a limit to this argument.
Content does not rescue a bad fit. It does not fix a wrong ICP. It does not make an unaffordable product suddenly affordable. It will not overcome a buying committee that has no real need.
What it can do is remove a specific failure, the one where a good-fit buyer decides in minute four that you do not understand their world.
That is the failure Karwatka’s post points toward, even if his prescriptions stay inside the meeting. Once you accept that enterprise deals are often decided before the second call, the leverage shifts. You stop treating content as decoration, and start treating it as sales infrastructure.
For technical founders, that is the more accurate frame. If you are running enterprise conversations without a sales team, your first job is not to sound persuasive on the call. It is to make the call feel like a continuation of useful work the buyer already did on your behalf.
Takeaway
If your deals die in the first two meetings, do not start by fixing meeting two.
Audit what a good-fit buyer can read about you before meeting one. If the answer is nothing, that is not a content gap in the abstract. It is likely the place where the deal first went cold.
Start there.
That is the argument Better Marketing is making, content is not only a demand lever, it is the precondition for a credible sales conversation.
For the source analysis that triggered this piece, see Karwatka’s enterprise deal post-mortem. For the adjacent founder-led sales conversation, see Don’t Delegate Your Fear. The cluster is clear. The gap is earlier than most people think.