The RFP Checklist for Evaluating AI Sales Vendors

Here is a usable checklist, not a framework you have to build yourself. It contains 15 questions across four categories: data and security, real integration versus slideware, adoption evidence, and exit terms. Score every AI sales vendor against all four before you sign anything.

Most checklists for this topic are written by a vendor, or by a site that earns a commission. This shapes which questions get asked and which get left out. This checklist has no product behind it, because SalesOS Labs doesn’t sell or resell sales tools.

Why most vendor RFP checklists are written by vendors

Read a few “AI sales tool evaluation checklist” posts and a pattern shows up fast. You will see leading questions that only one kind of answer satisfies. Categories are often weighted toward the sponsor’s strengths, and the exit-terms section is thin or missing entirely. That’s not always dishonest. It’s just what happens when the checklist author has a stake in the outcome.

The fix isn’t cynicism about every source. It’s running your own evaluation with a checklist built by someone who doesn’t care which vendor you pick. Then, verify answers yourself instead of taking a sales rep’s word for them.

This matters more in AI sales tools specifically than it did in the last generation of sales software. AI features are easier to demo well and harder to verify from the outside. A dashboard either does what it says or it doesn’t, visibly, in the first ten minutes of use. An AI feature can look impressive in a curated demo and behave completely differently against your actual data, edge cases, and volume. That gap is exactly what a real evaluation process is supposed to catch. It is also exactly what a vendor-written checklist has no incentive to help you find.

The four categories that matter

1. Data and security

• Where does our data live once it’s in your system, and who can access it?
• What’s your data retention policy after we stop using the tool?
• Do you train any model on our data, and can we opt out in writing?
• What certifications do you actually hold (SOC 2, not “SOC 2 in progress”)?

2. Real integration versus slideware

• Which specific fields sync with our CRM, and in which direction?
• Is that sync real-time or batch, and what’s the actual latency?
• What breaks if we change a field name or a stage definition on our end?
• Can you demo this against our instance, not a sandbox built for demos?

3. Adoption evidence

• What’s your customer logo count versus your active-usage count?
• What does a customer’s onboarding timeline actually look like, week by week?
• What’s the most common reason a customer churns or downgrades?
• Can we talk to a reference customer at our headcount and industry, not just any reference?

4. Contract and exit terms

• If we cancel, what happens to our data, our configurations, and anything we built inside your platform?
• Is data export included, or is it a paid service?
• What’s the actual notice period, and is there an auto-renewal clause we need to catch now?
• Is pricing locked for a term, or can it change at renewal without negotiation?

The exit-clause question almost nobody asks

Of everything on this list, the exit clause gets skipped the most. Nobody wants to think about cancellation while they’re excited about a new tool. However, this is where vendors have the least incentive to volunteer information. This makes it exactly the question you should ask directly and get in writing.

Specifically, ask what happens to your data and any build artifacts if you cancel. Build artifacts include workflows, sequences, or custom configurations you created inside the tool. Some vendors let you export everything cleanly. Others don’t, and you find out only when you try to leave.

Get the answer in writing, not verbally from a sales rep on a call.

Sales reps are often genuinely unsure of the answer themselves, or optimistic about it in ways the actual contract doesn’t support. If the master service agreement or terms of service is silent on data portability, assume the worst case. Negotiate a specific clause before you sign, not after you’ve built six months of workflows inside the platform.

How to run a “bring your own scenario” test instead of a scripted demo

A scripted demo is built to show the vendor’s best case. Ask instead for a session where you bring the scenario. This could be a real account from your CRM, a real objection your reps hear weekly, or an edge case that broke your last tool. Watch how the vendor handles something they didn’t script for. That tells you more in twenty minutes than an hour of prepared slides.

If you want a narrower, tactical version of this for the live demo moment specifically, that’s a companion topic worth reading before your next vendor call.

Weighting must-haves versus nice-to-haves

A checklist only works if the scoring isn’t cosmetic. Before you sit down with a vendor, separate your 15 questions into must-haves and nice-to-haves. A wrong answer to a must-have question disqualifies the vendor outright. A nice-to-have factors into the decision but doesn’t end it.

For most 51-200 person B2B teams, data handling and exit terms belong in must-haves. Integration depth and adoption evidence usually belong there too. Feature breadth and UI polish are more often nice-to-haves, even though demos are built to make you weight them heavily.

Write the weighting down before the calls start. It’s much harder to rationalize a bad exit-clause answer after you’ve already sat through an hour of a polished product tour.

A simple approach that works for most teams is to score each vendor 0 to 2 on every question. A score of 0 means the answer is a red flag, 1 means it’s acceptable, and 2 means it’s genuinely strong. Then, total the scores separately for must-haves and nice-to-haves. Any vendor scoring a 0 on a must-have question is disqualified regardless of how the rest of the sheet adds up. This keeps a charismatic sales team or a slick demo from overriding a real data-handling or exit-terms problem.

What we do differently

Most consultants who offer to run a vendor evaluation for you are either reselling one of the options or getting paid by the vendor you pick. SalesOS Labs takes no referral fees and resells nothing. This is what vendor-neutral AI consulting actually means in practice, not just as a tagline.

In practice, that means we join these evaluation calls with you. We ask the questions above (and the ones specific to your workflow) directly, in the room, instead of handing you a template and leaving you to run it alone.

Use the checklist before your next vendor call

Fifteen questions, four categories, no vendor’s fingerprints on the list. Run every AI sales vendor you’re evaluating through all four before you sign. Do not skip the exit-clause questions just because they feel like the least exciting part of the conversation. They’re usually the part that matters most a year later.