A companion checks the ledger, sorts the overdue invoices by age and amount, and writes each chase inside the existing conversation. Nothing sends until you have read it.
The chase has a known-good shape: a courtesy note before due, a reminder on the due date, escalating follow-ups at one week, two weeks and a month.
Every step is easy and the whole thing slips, because it is nobody’s favourite job. A weekly routine does not find it awkward.
01
What has to happen before each reminder sends?
A check that the invoice is still unpaid, a read of the last reply, and a judgment about tone.
Chasing a paid invoice costs more goodwill than the invoice was worth, and the reply saying "our AP portal needs a PO number" changes the next message.
A companion does all three per invoice. Chaser and Upflow put the cadence on rails with templated sequences and payment portals, and Xero and QuickBooks ship automatic reminders, as of this writing. Reading the replies is what a companion adds.
02
The chase, run weekly, drafted for you
Xero is native, so a companion starts from ledger truth: list overdue invoices, check nothing was paid this morning, sort by age and amount. It drafts each reminder in your voice inside the existing conversation rather than spawning reminder #4 as a cold email, and every draft pauses for approval.
Replies come back on the next run: a promised date gets logged and re-checked, a dispute gets routed to you. Full sequence: how to automate invoice chasing, with the collection variant at invoice collection.
03
Month three, measured
A 30-person agency, weekly routine, 14 overdue invoices. The companion verifies against Xero, drafts 11 reminders across three tiers, flags 2 as disputed for the account leads, and leaves 1 alone: the customer on the payment plan, per your standing instruction.
You approve the 11 in one pass. Eight weeks later average days overdue is down from 24 to 9, and the founder stopped spending Sunday evening on it.
04
Which overdue invoices actually get paid?
The forgotten ones, which is most of them.
A customer who genuinely cannot pay becomes a payment-plan conversation and a dispute becomes a call, and both arrive on your desk labelled instead of hiding inside the aged-receivables total.
Escalate tone gradually, reply within the existing thread, verify payment status before every send, and keep a person approving the drafts. A ledger check before each draft removes the two things that actually annoy people.
A Strawberry companion reads overdue invoices from Xero natively, drafts tiered reminders in your voice inside the existing threads, and every draft pauses for approval. Disputed invoices get flagged rather than nudged.
A courtesy note 3 days before due, a reminder on the due date, follow-ups at 7, 14 and 30 days overdue with escalating directness, then a call. Write the exceptions into the instruction once.
Strawberry fits teams whose chase is an email-judgment job on top of Xero: ledger read natively, every reminder drafted in the right thread, every send yours to approve. Chaser and Upflow sell payment portals alongside the cadence, as of this writing. Free to download, paid plans from $20/month.