Free vs paid software: when to upgrade

Start with the job the software must do, not the longest feature list.

Checks that matter

1. Stay free while it works.
2. Calculate time saved by paid features.
3. Check customer impact.
4. Compare competitors before upgrading.

Test the awkward part

Product demos show the happy path. Test the part of your workflow that usually causes trouble before committing.

Compare the real cost

Use the price of the plan containing the features you need, then account for users, contacts, usage, integrations and other add-ons.