Jeff BullasFast win (under 5 minutes): change any “7-day overdue” template to a “friendly reminder” that triggers after the due date for Net 30 (e.g., Day +5). Update the subject to: “Friendly reminder — invoice #{{INV}} due {{DUE_DATE}} (pay in one click).” Send it to yourself once to confirm links. That one tweak keeps tone calm and boosts response.
You’re right: cadence must match the terms. Let’s lock in a term-aligned sequence and add two AI upgrades that quietly increase collections without denting relationships: pre-due nudges and tone adaptation.
What you’ll need
- Invoicing/accounting tool with automations or an integration platform.
- Per-invoice payment link and a clear dispute/contact route.
- Clean customer contacts, listed payment terms, and a “strategic accounts” list.
- Basic AI access (any LLM) to generate/refine templates and tone variants.
Step-by-step setup
- Map your terms and set baselines. For each common term, define timing relative to the due date (not the invoice date):
- Net 15: Day -2 (heads-up), Day +3 (friendly), Day +14 (firmer), Day +30 (human).
- Net 30: Day -3 (heads-up), Day +5 (friendly), Day +20 (firmer with plan), Day +45 (human).
- Net 45: Day -5 (heads-up), Day +7 (friendly), Day +25 (firmer), Day +50 (human).
- Create a three-message sequence per term. Keep emails short, include invoice number, amount, due date, pay link, and a dispute link. Label the first two messages as “heads-up” or “friendly reminder,” not “overdue,” until you’re beyond ~10 days past due.
- Layer tone rules. Use “friendly” up to +10 days, “neutral/firmer” after that. For strategic accounts, stop automation after the second reminder and hand off to a human.
- Add a payment-plan offer trigger. If unpaid at Day +20 (Net 30), auto-offer a short plan (e.g., 50% now, balance in 14 days) via a simple reply or {PLAN_LINK}.
- Handle exceptions automatically. If an email bounces, create a task for a phone follow-up. If a reply contains dispute language (“incorrect amount”, “PO”, “credit”), pause reminders and route to a review queue.
- Test end-to-end on 10–20 invoices. Check deliverability, links, and that payments auto-reconcile to the correct invoice.
- Monitor and tune. Track open/click rates by step, days-to-pay after each reminder, and complaint rate. Adjust timing and subject lines accordingly.
Insider refinements that move the needle
- Pre-due heads-up works. A short Day -3 nudge reduces “oops, forgot” without sounding pushy.
- Subject line formula that converts: “Invoice #{{INV}} — {{AMOUNT}} — due {{DUE_DATE}} — pay in 10 seconds.” Clear, specific, action-oriented.
- Micro-intent link: add “Need a bit more time?” link that pauses automation and suggests a call or a plan. People appreciate the option.
- Quiet hours: schedule sends Tue–Thu mid-morning local time; it lifts response and reduces spam complaints.
Ready-to-use templates (Net 30 example)
- Day -3 (heads-up)Subject: Quick heads-up — invoice #{{INV}} due {{DUE_DATE}}Body: Hi {{NAME}}, a quick reminder that invoice #{{INV}} for {{AMOUNT}} is due on {{DUE_DATE}}. You can pay securely here: {PAY_LINK}. Questions or PO updates: {DISPUTE_LINK}.CTA: Pay now: {PAY_LINK}
- Day +5 (friendly)Subject: Friendly reminder — invoice #{{INV}}Body: Hi {{NAME}}, our records show invoice #{{INV}} for {{AMOUNT}} is now a few days past due. Here’s the one-click payment link: {PAY_LINK}. If anything looks off, tell us here: {DISPUTE_LINK}.CTA: Settle in seconds: {PAY_LINK}
- Day +20 (firmer with plan)Subject: Action needed — invoice #{{INV}} {{AMOUNT}}Body: Hi {{NAME}}, invoice #{{INV}} for {{AMOUNT}} is still open. You can pay here: {PAY_LINK}. If helpful, choose a short payment plan option: {PLAN_LINK} or reply to arrange dates.CTA: Resolve today: {PAY_LINK}
Copy-paste AI prompt (creates term-aligned sequences and tone)
You are an Accounts Receivable assistant. Given payment terms and a client profile, produce a 3-step reminder sequence with timing relative to the due date and short emails that match tone by stage. Requirements: 1) Align timing to terms (examples: Net 15, Net 30, Net 45). 2) Use “heads-up/friendly” before +10 days past due; firmer after. 3) Include placeholders {{NAME}}, {{INV}}, {{AMOUNT}}, {{DUE_DATE}}, {PAY_LINK}, {DISPUTE_LINK}, {PLAN_LINK}. 4) Output: a) a schedule list (e.g., Day -3, Day +5, Day +20) and b) three email templates with subject, 2–3 sentence body, and a one-line CTA. 5) Add a note with when to pause automation (on dispute/bounce) and when to route to human for strategic accounts.
Mistakes to avoid (and quick fixes)
- Calling it “overdue” too early. Fix: use “heads-up” and “friendly reminder” until at least +10 days.
- One-size-fits-all cadence. Fix: segment by terms and by account value; hand off strategic clients after the second reminder.
- Long emails. Fix: 2–3 sentences, then a clear CTA.
- Broken pay links or poor reconciliation. Fix: test invoice → payment → ledger matching before launch.
- Ignoring replies. Fix: route “help”, “PO”, or “dispute” keywords to a manual queue and pause the flow.
1-week action plan
- Day 1: Export invoices by terms; pick one term (Net 30) to pilot. Draft the three messages above.
- Day 2: Configure triggers relative to due date (Day -3, +5, +20). Add exception list for strategic accounts.
- Day 3: Set up bounce/dispute rules to pause and create tasks. Enable payment-plan link.
- Day 4: Send an internal test (10–20 invoices). Confirm deliverability, links, and auto-reconciliation.
- Day 5: Go live to a small cohort. Monitor opens, clicks, and payments.
- Day 6: Review tone complaints (aim for zero), adjust subjects and send times.
- Day 7: Compare days-to-pay vs. baseline and expand to the next term group.
Bottom line: match cadence to terms, keep messages short, and let AI handle tone and timing while you step in for exceptions. Do this well and you’ll speed up cash without sacrificing goodwill.