Integration with QuickBooks or Xero
The tool should read invoices, contacts and payments directly from your accounting system and stay in sync. Ask how often it syncs. A reminder sent an hour after a customer paid is the fastest way to annoy a good customer.
It reads replies, not only sends emails
Sending is the easy part. The work is in replies: a request for a copy, a question about one line, a new contact, a payment date. Ask what the tool does when a customer replies. If the answer is "it forwards to your inbox", then your team is still doing the collections.
Dispute handling
When a customer disputes an invoice, routine chasing should stop and the query should go to the person who can resolve it. A tool that keeps sending reminders through a dispute damages relationships. See our guide to invoice disputes for why.
Promise tracking
"We'll pay on the 15th" is one of the most common replies. Good software records that date, holds off until then, and follows up if nothing arrives. Without this, promises sit in an inbox and are forgotten.
Human approval
Check whether you can review and approve messages before they go, and decide which situations always come to a person.
Audit trail
Every email, reply, promise and change should be recorded against the customer and invoice. You need this when a customer says they were never told, when someone new picks up the account, or when you review a statement of account with a customer.
Reporting
You should see what is overdue, by how long, and what is being done about it: an accounts receivable aging report and a view of open promises.