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Name the customer job
Write down the first job the system must handle: contact records, a simple deal pipeline, lead capture, follow-up, support, or reporting. If the job is vague, a bigger plan will not fix the buying decision.
Separate free access from free capacity
Check the exact number of users, contacts, emails, forms, automations, reports, and credits included. “Free tools” describes an entry point; it does not mean every product feature or usage limit is free.
Count the people who need access
List the owner, sales users, support users, marketing users, and anyone who only needs reporting. Seat pricing and permission needs can change the real monthly cost quickly.
Test the handoff
Put one real inquiry through the workflow. Confirm who receives it, where it is stored, what reminders exist, and how a person can correct an inaccurate record.
Check migration and ownership
Before importing contacts, identify export options, field mapping, duplicate handling, account ownership, and the process for removing a user without losing business history.
Price the next twelve months
Include seats, contacts, credits, add-ons, onboarding, migration, implementation time, renewal terms, taxes, and the cost of changing plans later. Compare the total with the value of the job it replaces.
Define the upgrade trigger
Upgrade when a measured limit blocks a valuable workflow or the saved time and recovered opportunities justify the cost. Do not upgrade because a feature page makes the larger plan feel safer.