Timing is the second decision, and in a school the calendar decides it for you. The gaps between terms, and the summer break in particular, give you a window to move without a live term relying on the switch. Avoid cutting over in the middle of admissions or reporting season. Agree a clear go-live date, keep the old system readable for a defined period afterwards, and confirm you can still retrieve historic records if you need them. Never delete the old data until the new system is verified and signed off.
The licence fee is the number on the quote. The total cost of ownership is the number a school business manager actually has to plan for, and the two are rarely the same. Before signing for any school management information system, it pays to map every cost across the full contract, not just year one.
Then look for the fees that hide between the lines. Common ones include charges for extra modules, for additional user accounts, for integrations with other tools, for data exports, and for support above a basic tier. Payment processing fees on parent transactions can add up quietly across a year, so ask exactly how those are charged and who absorbs them. None of these are unreasonable in themselves; the problem is only when they are not disclosed up front.
For more detail, see Compass Education School MIS.
Certification is the second, more concrete checkpoint. ISO 27001 is the recognised international standard for information security management, and a vendor holding current certification has had its security controls independently audited against that standard rather than simply asserting they are secure. For any part of a system handling payment data, such as fee billing or canteen top-ups, PCI-DSS Level 1 compliance is the equivalent standard specifically for payment card handling, and it is worth asking whether that certification covers the billing module directly rather than being described only at the level of the parent company.
The cheapest headline price often is not the cheapest system to own. Ask for every cost in writing, model the full term, and compare providers on the total rather than the quote. That is the figure governors will ask about, so bring it to the table first.