Most nonprofits do not have a software problem so much as an inventory problem. Tools get added one at a time, each solving a real need in the moment, and a few years later nobody on staff can say with confidence exactly what the organization pays for, when each contract renews, or who actually uses each seat.
Before any consolidation conversation is worth having, do the audit first. It takes an afternoon and it changes every conversation that follows.
Once the list exists, a short round of vendor questions usually surfaces the real cost of staying put: what does the next tier of seats cost, what is not included in the base price, and what would it take to export everything you own if you left.
The point of the audit is not to justify switching. It is to know, in writing, what staying costs.
Two patterns show up again and again once organizations do this exercise: a handful of tools nobody remembers approving, and two or three systems quietly doing the same job for different teams. Neither is a surprise once you see it in one place — it is only invisible when it is spread across seven different invoices.
A migration checklist built around the nonprofit calendar, from data cleanup through parallel run and cutover.
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