Guide
Sixteen questions to ask every vendor — us included
Most buyer's guides are rigged so the author wins. This one names the places we lose, because a checklist you cannot use against its author is not a checklist.
Buying business software is mostly an exercise in asking questions whose answers do not matter until much later. The demo shows you the parts that work. What decides how the next three years feel is ownership, pricing shape, access control, and what happens when something goes wrong.
Use this against us too. We answer some of it well and some of it badly, and the page says which.
Ownership and exit
Ask these first. They are the cheapest questions to ask and the most expensive to get wrong.
“If we leave, what exactly can we take?”
A CSV of contacts is not the same as your books, your documents and your website. Ask for the specific list, not "of course you can export".
“Who holds the money?”
If payments settle into the vendor’s account and are paid on to you, then a dispute, an outage, or their bad quarter is your cash-flow problem.
“Do we own the front end?”
A page builder inside a subscription is rented. Source code in your own repository is owned. The difference only becomes visible on the day you want to leave.
“What happens if you are acquired or shut down?”
Small vendors do not like this question, which is why it is worth asking. Listen for a concrete answer rather than reassurance.
Pricing shape, not price
The number matters less than what it scales with. A cheap price on the wrong metric gets expensive in exactly the way that hurts.
“What does the bill scale with?”
Seats, contacts, revenue, usage? Whatever it is, you will end up avoiding it — so make sure it is something you do not mind avoiding.
“What will this cost when we double?”
Ask for the number, not the tier name. Then ask what happens in a slow quarter, because that is when it actually gets tested.
“Does adding a user cost money?”
If yes, you will ration logins, and the people you ration are usually the ones whose work is least visible to you already.
“Are we billed or do we pre-pay?”
An invoice you can dispute is a relationship. A balance you top up is a transaction. Know which one you are entering.
Access and accountability
These get asked after the first incident. Ask them before.
“Can permissions follow our actual org chart?”
Fixed role lists break the moment you have two locations or one part-timer. Ask what happens when you restructure.
“Can we tell who saw what, and when?”
"Who could see this?" is a question with a deadline attached. Either the system answers it or somebody spends a week guessing.
“Can a record be edited away?”
Ask specifically about financial history. Software that can quietly rewrite its own past cannot help you prove anything.
“What can an integration or AI assistant reach?”
If the only credential available does everything, then every integration is a full-access integration. Ask whether access can be granted narrowly.
The questions that only matter later
Nobody asks these in a demo, and they decide how the next three years feel.
“How do updates reach us?”
Automatically, on their schedule, breaking our customizations? Or when we choose, without losing our work? Ask what happened to the last customer who customized heavily.
“What happens if we do not upgrade for six months?”
A good answer is specific. A vague one means nobody has tried it.
“Can our own developers build on it?”
Ask whether the API is documented, whether fields ever get removed, and what a breaking change looks like when it happens.
“What are you bad at?”
The single most informative question on this page. A vendor who cannot name a weakness either does not know their product or is willing to mislead you — and you will find out which after signing.
Where we lose
Since the last question is the important one, ours: you cannot control the database schema — the data layer is not yours to invent, and if that is the point of your project we are the wrong choice. A large enterprise sales organization with a customized process and staff to run it should buy a dedicated CRM. And if you spend heavily across many ad platforms and run on incrementality testing, a specialist attribution product beats ours.
We are strongest for a business that wants one system that genuinely fits together, owns its own data and front end, and does not want to ration logins.