10 Questions to Ask a Software Vendor Before You Sign

A vendor running a demo for you is selling. The sooner you sign and stop asking things, the better their week goes. Ask these anyway.

1. Who Owns the Code?

Why it matters: You paid for custom development, so what came out of it should be yours. A vendor who owns it can bill you licence fees forever, sit on your workflow the day you want to leave, or shut the service down with your operations inside it. Standard SaaS works differently and that’s fine. Custom code belongs to you.

Ask: Does the vendor own the source code, or do I? If they own it, what happens when they go out of business or shut the service down?

2. What Happens on Day 91 if I Cancel?

Why it matters: Vendors usually let you export your data for a window after you cancel, which might be 30 days or might be 90. After that it’s gone. Find out exactly what comes back to you, and exactly how long you have to grab it.

Ask: If I cancel my subscription tomorrow, what data can I export? In what format? How long do you keep it? What does it cost?

3. Where Does My Data Live?

Why it matters: Job data and client details sitting on servers in a country you don’t do business in can create legal exposure for you. If the vendor gets hacked, your recourse might be nothing at all. Some of your own client contracts may also require you to disclose where their information is held.

Ask: Which countries store my data? Can I request it be stored in Canada? What’s the cost if you don’t offer it? Does the vendor comply with Canadian privacy law?

4. What’s the On-Call Arrangement When It Breaks at 2am Saturday?

Why it matters: When the tool dies in the middle of your busiest hours, you need to know who picks up the phone and when. SaaS support comes in tiers. A paid plan might get you an answer within 24 hours, or it might get you a ticket number.

Ask: What’s your response time guarantee for critical issues? What counts as critical? What’s the cost for faster response?

5. Can I Export Everything, and How?

Why it matters: No tool should be able to trap you. You want a clean export of all of it, in a portable format like CSV or JSON that another system can read, so you can move whenever you decide to.

Ask: Can I export all my data? How frequently? In what format? Without paying extra?

6. What’s Your Billing Model When Scope Changes?

Why it matters: Some vendors bill by the user, some by how much data you store, some by transaction volume. Grow the business and you can find the bill has doubled or tripled. Know how the price moves as you get bigger, before you’re locked in.

Ask: How do you price as I add users, data, or volume? Are there hard caps or surprising step-ups in cost?

7. Do You Have Dependencies on Other Third-Party Services?

Why it matters: If the vendor runs payments through Stripe or SMS through Twilio, a bad afternoon at Stripe or Twilio becomes a bad afternoon for you. Find out what sits underneath the product, and what the vendor does when one of those pieces falls over.

Ask: What other services does your platform depend on? What happens if they go offline? Do you have a backup?

8. What’s the Data Retention and Compliance Policy?

Why it matters: Handling client information means knowing whether the vendor keeps backups, which they should, and for how long they hold them. You also need to know whether they meet PCI for payment card data, PIPEDA for privacy in Canada, or any other standard you’re held to.

Ask: How long do you retain deleted data? Do you have backups? Are you PCI compliant? PIPEDA compliant? Can you provide a SOC 2 report?

9. Can I See the Service Level Agreement and Support Terms in Writing Before I Sign?

Why it matters: A salesperson saying “we’ll respond in one hour” is worth nothing once the contract says otherwise. If it isn’t written down, it doesn’t exist. Get every important promise on paper.

Ask: Can I review the SLA? The support terms? The data retention policy? I’m not signing anything without seeing all of it.

10. What Happens If a Much Larger Company Buys You?

Why it matters: The vendor you like today can get bought by a company with no interest in your trade, and that buyer might kill the product or raise the price hard. Find out where an acquisition leaves the customers who are already paying.

Ask: If your company gets acquired, what happens to existing customers? What if the acquirer decides to sunset the product?

The Real Test

Send all ten in writing and get written answers back. Evasion, slow replies, or a friendly gloss over the details tells you plenty about the next three years. A vendor worth using answers every one of them straight, because they know they’re asking for your trust and your data.

Every demo looks great. What binds you is the contract, so read that one carefully.