Othmane Khadri recently shared something that caught my attention: "Should you ever go over someone's head to close a deal?" He described a founder selling sales tech with a sales manager as the champion, end users in the sales team, and multiple stakeholders involved. The temptation on the table was simple: skip the messy middle and "go straight to the CEO to force the deal through."

I have seen that move get celebrated as "executive access" or "being proactive." But Othmane's argument cuts through the ego boost: for early-stage companies, this is often one of the fastest ways to create a customer that pays you and then never truly uses you.

"Your deal's value equals money + feedback loop. And that feedback loop is worth 10x more than the contract value."

That line is the heart of the whole post. If you are pre-PMF (or early PMF), the contract is not the finish line. The learning is. And when you try to force a deal from the top, you often destroy the very conditions required to learn.

The hidden cost of "closing" by going over someone's head

Othmane laid out a chain reaction that happens when a CEO forces a tool onto a team that did not ask for it. It is worth expanding because each step is a predictable adoption failure pattern.

1) The end users see you as the villain

In B2B, your product is not adopted by an org chart. It is adopted by humans with habits, pride, and existing workflows. When the message lands as "Leadership bought this, now use it," the vendor becomes the symbol of disruption imposed from above.

Even if your product is objectively better, the emotional starting point matters. Adoption is not just feature-value fit. It is change-management fit.

"The sales team sees YOU as the villain."

A forced tool creates a compliance mindset. People do the minimum, click around once, then return to what already works. They will blame the product for every ounce of friction because the product represents lost autonomy.

This is especially brutal in sales teams, where time is the scarce resource and skepticism is a learned defense mechanism. If the tool was not chosen with them, they will assume it was chosen against them.

3) You undermine your champion and create internal politics

Othmane highlighted a subtle but deadly dynamic: if your champion is the sales manager, and you bypass them to the CEO, you are not just accelerating a decision. You are publicly signaling that your champion was not enough.

"The sales manager your supposed champion just got undermined in front of their team."

Now your champion has less credibility, less ability to drive behavior change, and less willingness to go to bat for you when issues pop up (and issues always pop up early).

4) You also create doubts in the CEO's mind

This is the part most sellers miss. Even if the CEO signs, the CEO can simultaneously lose confidence in the priority level of the initiative. Othmane put it plainly: the CEO starts thinking, "Wait I thought you said this was a priority. Why did I have to step in?"

So you end up with a deal that is "closed" but politically orphaned. No one truly owns it day-to-day.

Why this is extra dangerous pre-PMF

If you are early, you are not just selling software. You are building a learning engine. You need fast iteration cycles with real users, real data, and honest feedback. Forced adoption breaks that engine.

Othmane's framing is useful because it redefines what a deal is worth. Revenue is obvious. The feedback loop is the compounding asset.

Here is what gets lost when adoption is dead on arrival:

Usage data that reveals where your onboarding fails
Qualitative feedback on missing workflows
The "what's magic" moments you can double down on
Internal case studies you can turn into positioning
Champions who can become references

And there is another loss: expansion. A team that resents you will not introduce you to adjacent teams. They will actively warn others off.

"Congratulations. You 'closed' the deal. But you killed adoption. You killed your feedback loop."

The alternative: bottom-up conviction, then top-down alignment

What I like about Othmane's advice is that it is not anti-CEO or anti-executive. It is sequencing. He is arguing for earning the right to go top-down by first proving value bottom-up.

Step 1: Win end users first

If the end users are the sales team, make them the center of your process. Do not treat them as a box to check after procurement. Treat them as the product's real customer.

Practical ways to do this:

Run a short pilot with a small group of reps (2-5)
Get them to a clear "first win" within 7-14 days
Build a lightweight success plan around their workflow, not your feature list
Capture specific quotes and before-after metrics (time saved, meetings booked, fewer manual steps)

The goal is not demos that impress. The goal is daily usage that sticks.

Step 2: Arm your champion with proof

Othmane described the right internal dynamic: "Use their conviction to arm your champion with a successful internal case."

This is where many founders can level up. Instead of sending your champion a generic ROI deck, give them ammunition that matches how decisions are made internally:

A one-page summary of rep results
A screenshot of a workflow that removed pain
A short list of objections and how users answered them
A rollout plan that reduces risk

When the champion can say, "The team asked for this," you are no longer selling against inertia. You are channeling momentum.

Step 3: Let users sell it up

This is the most counterintuitive part for founder-sellers who are eager to control the process. But it works because it aligns incentives.

When the request comes from the field, leadership interprets it as signal, not noise. The tool becomes a lever for performance, not a pet project.

"Let THEM sell it up. That's how you build a deal that sticks."

When is it OK to go to the CEO?

Othmane made an important nuance: there are scenarios where the middle layer blocks progress even though end users love the product. In that case, going to the CEO can be appropriate, but only with the right intent and framing.

The difference is "force" versus "serve."

A simple test

Ask yourself: if I bring this to the CEO, am I asking them to override their team, or am I sharing what their team is already saying and asking for help aligning priorities?

Othmane's version is clear: you go to the CEO "not to 'force' the deal but to share what their own team is telling you."

That conversation sounds like:

"Your reps are getting value and want to expand usage"
"Here are the outcomes they saw in the pilot"
"Here is what is slowing rollout"
"Can we align on ownership, timeline, and what success looks like?"

This approach protects the champion while still leveraging executive sponsorship.

A quick checklist to keep deals from becoming shelfware

If you want a practical way to apply Othmane's playbook, I would use this checklist before you escalate above your champion:

Do we have at least 2-3 power users who would complain if the product disappeared?
Can those users articulate value in their own words?
Is there a credible internal owner for rollout (enablement, ops, manager)?
Have we documented a small, repeatable success path?
If we talk to the CEO, are we asking for alignment and resources, not an override?

If you cannot check the first two boxes, escalation is usually just a way to hide a weak value story.

Closing thought

Othmane's core message is a reminder that "closing" is not the same as winning. Especially early on, the real win is adoption that creates learning, learning that creates product improvement, and product improvement that makes future selling easier.

Bottom-up conviction. Top-down alignment. That sequencing is the play.

This blog post expands on a viral LinkedIn post by Othmane Khadri, AI native GTM agency. View the original LinkedIn post ->