What to Ask Your AI Vendor: 25 Questions Before Signing an Enterprise Contract
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What to Ask Your AI Vendor: 25 Questions Before Signing an Enterprise Contract

The AI vendor market is crowded with great slide decks and mediocre products. Here is how to tell the difference before you sign the contract, not after.

WS

Wael Salem

Author

March 20, 2026
12 min read

What Separates Real AI Vendors from Slide Decks

The AI vendor landscape right now is a mess. Everyone has a pitch deck with the word "intelligence" in it. Everyone claims enterprise-grade. Everyone has a case study that sounds impressive until you realize the "enterprise client" was a three-month pilot that never went to production.

Here is how to cut through it.

The Product Questions

Start with what the product actually does, not what the roadmap promises.

Show me the product running on real data. Not a demo environment with curated data. Your actual data. Or at minimum, data that resembles your actual use case in complexity and messiness. A demo on clean data proves nothing about production performance.

What happens when the input is garbage? Every real-world dataset has missing fields, inconsistent formats, and edge cases. How does the system handle bad data? Does it fail gracefully? Does it flag issues? Or does it silently produce wrong outputs? This question alone eliminates a surprising number of vendors.

How does the system handle cases it has never seen? Novel inputs are inevitable. Does the AI acknowledge uncertainty? Does it have a confidence threshold below which it escalates to a human? Or does it confidently hallucinate an answer? This is the difference between a production system and a toy.

What is your model update cycle? How often do models get retrained or updated? What triggers an update? Can the customer control when updates are applied? A vendor that pushes model updates without customer control is a vendor that can break your workflow without warning.

Can I see the system under load? Not theoretical throughput numbers. Actual performance at the volume you expect to run. Latency, accuracy, and resource consumption all change at scale. If the vendor has only tested at small scale, you are their beta test.

The Architecture Questions

These determine whether the product will actually survive in your environment.

Where does my data go? During inference, during training, during storage. Draw me the data flow diagram. If they cannot do this on the spot, they have not thought about it carefully enough.

Can this run in my environment? Not "can it theoretically run" but "have you actually deployed in a similar environment?" Cloud, on-premise, hybrid, air-gapped -- the answer matters, and "we can adapt" is not the same as "we have done this."

What are the dependencies? What external services does the system call? What happens if one of those services goes down? A system that silently fails when an external API is unavailable is a liability.

How do you handle multi-tenancy? If you are on a shared infrastructure model, how is your data isolated from other customers? Logical isolation? Physical isolation? What are the guarantees?

The Business Questions

This is where you find out if the vendor will be around in two years.

How many production deployments do you have? Not pilots. Not POCs. Production. Running in an enterprise environment with real users and real consequences. If the number is small, that is not necessarily disqualifying, but you should know what you are signing up for.

What does your customer retention look like? Vendors that deliver value keep their customers. If they dodge this question, draw your own conclusions.

What is your pricing model and how does it scale? Understand the unit economics at your expected scale, not just the introductory pricing. Some models that look cheap at low volume become expensive quickly. Make sure you understand what you are paying for at the scale you expect to reach.

Who owns the models trained on my data? If the vendor is using your data to improve their general model, you need to know that upfront. Some organizations are fine with it. Some are not. But nobody should be surprised by it after signing.

What happens if we want to leave? Data portability, model portability, transition support. The best vendors make it easy to leave because they are confident you will not want to. The worst vendors make it hard because they know you might.

The Red Flags

Here is what should make you pause during an evaluation:

The vendor cannot show you a production deployment without heavy caveats. The vendor talks about their technology more than your problem. The vendor gets defensive when you ask about failure modes. The vendor's pricing requires a "custom quote" conversation that they keep delaying. The vendor cannot provide references from customers in your industry.

None of these are automatic disqualifiers. But stack three or four of them together and you are looking at a vendor that is not ready for your use case.

The Bottom Line

The best AI vendors are not the ones with the most impressive demos. They are the ones who can have an honest conversation about what their product does well, what it does not do yet, and what the realistic timeline to value looks like for your specific situation.

We try to be that kind of vendor. If you want to evaluate SV Labs products with this lens, reach out to info@salem.ventures. We will give you straight answers.

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