Guide
10 Questions to Ask Any Software Vendor Before You Commit
Critical questions about data ownership, exit plans, support, and billing that vendors count on you not asking.
When a vendor is pitching their software to you, they’re selling. They want you to sign the contract and stop asking questions. These are the questions you need to ask anyway.
1. Who Owns the Code?
Why it matters: If you pay for custom development, you should own what gets built. If the vendor owns it, they can charge you licensing fees forever, hold your workflow hostage if you want to leave, or shut the service down and you lose everything. Standard SaaS is fine. Custom code should be yours.
Ask: Does the vendor own the source code, or do I? If they own it, what happens if they go out of business or shut down the service?
2. What Happens on Day 91 if I Cancel?
Why it matters: Most vendors will let you export data, but only for a limited time. Sometimes it’s 30 days. Sometimes 90. After that, your data is gone. You should know exactly what you get back and exactly how long you have to retrieve it.
Ask: If I cancel my subscription tomorrow, what data can I export? What format? How long do you keep it? What’s the cost?
3. Where Does My Data Actually Live?
Why it matters: If your job data and client information is stored on servers in a country you don’t do business in, you might have legal exposure. You might not have recourse if the vendor gets hacked. You might violate your own client contracts if you don’t disclose it.
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: If the tool goes down during your busiest business hours, you need to know who picks up the phone and when. Most SaaS vendors have tiered support. You might get a response in 24 hours on a paid plan. You might not.
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: You should never be trapped by a tool. You need a clean export of all your data in a standard format (CSV, JSON, something portable) so you can move it elsewhere if you need 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 charge by the user. Some by the amount of data you store. Some by transaction volume. If your business grows, will your bill double? Triple? You need to know upfront whether the pricing scales reasonably with your growth.
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’s system depends on Stripe for payments, or Twilio for SMS, or some other third party, and that third party goes down, your system goes down too. You should know what dependencies exist and what the vendor does if a dependency fails.
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: If you handle client information, you need to know if the vendor keeps backups (they should) and for how long. You also need to know if they comply with PCI (payment card data), PIPEDA (privacy law in Canada), or other standards you might need.
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: Verbal promises are worth nothing. If a vendor says, “We’ll respond in one hour,” and it’s not in the contract, it doesn’t exist. Everything important needs to be in writing.
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 You Get Acquired or Acquired By a Much Larger Company?
Why it matters: A vendor you like might get bought by a larger company that doesn’t care about your vertical anymore. They might kill the product. They might raise the price dramatically. You should know what happens to existing customers if the vendor gets acquired.
Ask: If your company gets acquired, what happens to existing customers? What if the acquirer decides to sunset the product?
The Real Test
Ask these questions in writing and get written answers. If a vendor is evasive, slow to respond, or tries to gloss over the details, that’s a red flag. The vendors worth using will have clear answers to all ten questions because they know they’re asking for your trust and your data.
Don’t let a slick demo trick you into forgetting these. The demo works great. The contract is what matters.
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