The SaaS Buying Checklist

Before you look at vendors

Define the job in one sentence: 'We need software that does X for Y people.' If you cannot, you are not ready to evaluate.

Write down three to five must-haves and your hard constraints: budget ceiling, team size, must-have integrations, and any compliance requirements. Everything else is a nice-to-have — treat it that way during demos.

During evaluation

Always trial with real work, not vendor demo data. The goal is to find friction before you sign, not to confirm the sales pitch.

Ask who will administer the tool and how much time it takes. Software that needs an owner nobody has time to be will decay within a quarter.

Check the pricing page yourself rather than relying on quotes: understand what triggers an upgrade — seats, usage, contacts, or a gated feature you will eventually need.

Security and data questions

For anything touching customer data, review the vendor's official security and privacy documentation: data location, retention, subprocessors, and whether your data trains their AI models.

Verify compliance claims on the vendor's own trust or security pages. Do not accept a badge on a review site — including ours — as evidence of certification.

Before you sign

Confirm the exit path: can you export your data in a usable format, and what happens to it after cancellation?

Check renewal terms — auto-renewal windows and price-increase clauses are where SaaS budgets quietly break.

Start annual only after a successful trial period; month-to-month is cheap insurance on an unproven tool.