You can have the best product in the market and still be unbuyable

You finally get the meeting. Your internal sponsor on the buyer side is excited. Then the purchasing team loops in security and asks for proof. The deal slows down.

Most founders treat that moment like an annoying formality. They assume it is just paperwork, or something you can smooth over with a few policies and a confident call. That assumption is why enterprise deals stall.

What I did not appreciate early on is that security is not only about risk. In enterprise buying, it is also a filter. It decides who even gets to compete.

When I say “security proof,” I mean simple, concrete receipts: short documents, screenshots, reports, and explanations that show what you actually run today. Not what you plan to do later.

What is actually happening in enterprise buying

When an enterprise evaluates your product, they are not only asking, does this solve the problem. They are also asking, what happens if this goes wrong, who gets impacted, and who is accountable.

If your product touches sensitive customer data or sits inside an important business process, security stops being a nice to have and becomes part of the selection criteria. That is especially true when the tech is new or changing quickly. During the recent wave of companies rushing to adopt AI tools, security got pulled into vendor selection earlier and more often, because uncertainty was high and the downside was unclear.

In practice, the process looks like this. The business team wants speed and capability. Security wants to see that the risk is understood and managed. Procurement wants standardization and a clean paper trail. You might be competing against multiple vendors at once, including mature vendors and smaller teams that move faster. At that point, security is not judging your intent. They are judging whether you look safe to deploy and support in the real world.

The misconception: security only matters at the end

A common misconception is that security is something you deal with after you win the business side. Founders think the buyer will push it through, then you can tidy things up later.

In many enterprise environments, it does not work that way. Security review is often a gate, not a checkbox. If the reviewer cannot build trust quickly, they will delay the evaluation, narrow the scope, or recommend a safer alternative. That recommendation carries weight because it reduces future headaches for everyone involved.

The irony is that the security team is usually not trying to be difficult. They are trying to avoid being the person who approved the vendor that caused a breach, a customer incident, or a messy audit finding.

Proof beats confidence. Every time.

When I was on the buyer side, I would ask vendors for whatever security materials they had, then review them before the call. Some had third party reports. Some had a simple security overview. Some had nothing. Even when a vendor did have a report, the reality behind it varied wildly.

You can usually tell the difference between a real security program and a performance pretty fast. Mature vendors tend to have safeguards that generate proof by default. Less mature vendors lean on manual processes, spreadsheets, and people remembering to do the right thing. That is fragile, and reviewers know it.

And then there is the third category. Teams with little to no safeguards at all who are genuinely surprised you are asking. They assume “we are small” is an acceptable risk argument, or that saying “we take security seriously” is enough. It is not.

If you cannot show who has access, how you control access, how you update systems, how you back up data, and how you would notice a problem, the buyer has nothing solid to stand on internally.

One pattern came up constantly. A startup would describe a “plan for incidents” that sounded fine until you asked how they would notice an incident in the first place. The plan would boil down to “we will shut off access when we find out.” Then you ask what signals tell you something is wrong, what monitoring exists, what alerts are configured, and who is responsible for responding. If the answers are vague, trust drops immediately. Not because the people are bad, but because the system is not there.

This is the core point. Enterprise security reviewers are not looking for perfection. They are looking for believable signals that you can operate safely when things get messy.

The tradeoff founders need to accept

If you want enterprise revenue, you are opting into enterprise expectations. That does not mean you need a huge security team or gold plated compliance. It does mean you need to choose where to be strong, and you need to be honest about what is not there yet.

Here is the tradeoff. If you invest early in a baseline of safeguards and reusable proof, you move faster later. If you delay, you will pay the tax during every deal, because each customer will force you to re explain your story from scratch while your team scrambles to patch gaps under pressure.

The best part is that these investments compound. A clean inventory of devices and cloud assets makes updates and patching easier. Strong access controls reduce incident risk and also make audits easier. Centralized logs help you notice problems and also strengthens your credibility when you explain how you would respond.

When the smaller vendor still wins and how to make that safe

Sometimes the smaller vendor has the only product that fits the use case. Enterprises do choose them, but rarely with a handshake and hope. They choose them with conditions.

If you are that smaller vendor, expect two things. First, the contract may include security requirements with a timeline. Second, someone on the buyer side may actively work with you over months to get you to an acceptable baseline, because they want the product but they cannot justify the risk otherwise.

This is where founders can turn security into value. You can make it easy for the buyer to say yes by being structured about how you close gaps. That looks like a clear plan, predictable milestones, and proof that shows progress without drama.

What surprised me was how often a strong product lost for completely avoidable reasons. Sometimes the vendor could not explain their security setup clearly. Other times, they had almost nothing in place and did not realize that would disqualify them. Either way, the buyer will pick the option that feels safer to adopt and support.

Practical next step: build the baseline that makes progress predictable

If you are not selling to enterprises yet, this is still worth doing now, because you will reuse it later. If you are already selling, this will reduce deal friction and reduce the amount of custom work you do per customer.

Write a one page security overview that explains your environment, how you handle data, and the safeguards you operate today. Keep it plain language and specific.

Pick a small set of safeguards that produce proof by default, like strong access control, device and account inventory, a regular update and patch routine, backups with restore tests, and basic logging. Make sure each one has something simple you can show.

Create a lightweight evidence folder with screenshots, reports, and short runbooks that you update monthly or quarterly. The goal is not volume. It is consistency.

Rehearse your “when things go wrong” story end to end, including how you notice issues, how you confirm what happened, how you stop the damage, how you communicate, and how you prevent repeats. If your ability to notice issues is weak, fix that first because everything else depends on it.

Decide what you will commit to contractually if needed, including timelines for closing gaps, and make sure you can actually deliver those commitments.

Where this is going next

Enterprise security teams are getting less patient with vague assurances, especially for tools that touch sensitive data or automate critical workflows. Buyers are also getting better at comparing vendors quickly. The ones who win are not always the ones with the most documents. They are the ones who can show that security work is real, repeatable, and improving.

If you want to get ahead of it, focus on building reusable proof and a baseline you can defend calmly. You are not doing this to impress anyone. You are doing it so enterprise deals feel less like a one off interrogation and more like a predictable evaluation you can pass without heroics.

If you want help getting there, we can take the same baseline safeguards enterprises expect and actually implement them with you, then turn the result into a simple roadmap and an evidence pack you can reuse across deals. That way you are not just explaining security. You are steadily building it, and making progress predictable.