Automated Invoice Reminders

The Follow-Up Email You Always Forget to Send — Sent Automatically, Every Time

The average unpaid invoice gets chased two or three times before it's collected. Each chase is 5–10 minutes of real time — drafting the email, looking up the contact, waiting for a reply. Multiply that across your open AR and you're spending hours a week doing work that a machine should be doing. Win! sends a timed sequence of polite, branded follow-up emails on every unpaid invoice — before the due date, on the due date, and at overdue intervals you control. Every reminder includes a one-click Pay Now link. Reminders stop automatically the moment payment arrives.

30-day free trial · No credit card required

Why a timed reminder sequence outperforms a one-off follow-up

Most businesses send one reminder, wait, and then give up or call. Win! sends a predictable sequence at exactly the right moments — just before the due date when the customer still has time to act, on the due date when they feel the urgency, and at escalating intervals when the invoice is overdue. Each message has a direct Pay Now link that takes the customer to checkout in one click. The sequence works because it's relentless in a professional way — and it stops the moment the problem resolves.

The Win! reminder sequence

Fully configurable. Win! suggests sensible defaults — you can adjust the timing and copy for each stage. Enable as few as one or run the full sequence.

3 days before due

Friendly heads-up

A gentle reminder that the invoice is due soon — the customer still has time to act and the tone is accordingly relaxed. The Pay Now link is prominent. This is the reminder that catches customers who just forgot and want to stay on good terms with you.

On due date

Polite notice

The invoice is due today. Still professional and courteous — this is a courtesy, not a demand. Includes the full invoice amount and a direct payment link. Most customers who were planning to pay do so at this stage.

7 days overdue

Firm follow-up

A firmer follow-up with the overdue amount clearly highlighted. Mentions that payment is now past due and asks the client to settle today. The tone shift is intentional — this message is designed to prompt action, not just awareness.

14 days overdue

Escalation notice

A direct communication noting the invoice is significantly overdue. This stage almost always prompts a response — payment, a dispute, or a conversation — that ends the cycle. You stop spending time chasing and start spending time resolving.

Invoice paid

Reminders stop automatically

The moment payment is received — through the reminder link, autopay, direct bank transfer, or any other channel Win! detects — all pending reminders for that invoice are cancelled immediately. You will never accidentally chase a customer who has already paid.

What makes Win! reminders different

These aren't generic notification emails. They're conversion-optimised payment prompts that look like they came from you and remove every friction point between intent to pay and payment received.

One-click Pay Now link in every email

Every reminder contains a direct link to a branded checkout page. Customers click, enter their card or bank details, and pay — no login, no account creation, no friction. You get paid within minutes of a reminder being opened, not hours or days.

Reminders stop automatically on payment — from any source

The moment Win! detects a successful payment — whether it came through the reminder link, AutoPay, a bank transfer, or even a manual mark-as-paid in your accounting platform — all pending reminders for that invoice are cancelled instantly. Clients never receive a chaser after paying.

Fully branded — looks like it came from you

Every reminder email carries your company name, logo, and primary brand color. To your client it looks like a professional email from your business — not from a third-party payment platform. Reply-to goes directly to your email address.

Works alongside AutoPay with no overlap

AutoPay-enrolled customers never receive reminders — their invoices charge automatically. Reminders are only sent to non-enrolled customers. The two systems coexist in Win! without any configuration needed — the right action happens for every client automatically.

Reminder FAQ

Can I customise the reminder schedule?+

Yes. Win!'s automation settings let you configure the timing (days before/after due) and choose which stages to activate. You can enable as few as one reminder or the full four-stage sequence. You can also customise the subject line and body copy for each stage.

Can I turn reminders off for specific clients?+

Yes. You can disable automated reminders on a per-client basis from the client detail page in your dashboard. This is useful for clients you prefer to handle personally, or those enrolled in AutoPay who don't need reminders.

Do reminders work with Xero and QuickBooks Online?+

Yes. Win! syncs invoices from both Xero and QuickBooks Online. Reminders fire based on the due date set in your accounting platform — whatever date is on the invoice in Xero or QBO is what Win! uses.

What if a client disputes an invoice?+

Win! surfaces disputes in your dashboard. You can pause reminders on a specific invoice while the dispute is resolved — a single toggle stops all future chasers on that invoice without affecting reminders on other invoices for the same client.

Will reminders embarrass me if a client has already paid?+

No. Win! checks payment status in real time before each reminder fires. If the invoice is paid — by any method, including outside of Win! — the reminder is cancelled automatically. You never send a chaser to someone who has already settled the invoice.

Let Win! do the chasing. You have better uses for your time.

Connect Xero or QuickBooks, link Stripe, and Win! starts monitoring your invoices immediately. The next overdue invoice gets a perfectly-timed reminder — with a Pay Now link — without you lifting a finger. 30-day free trial, no credit card required.

Also see: AutoPay invoices · Xero + Stripe

Legal disclaimer: This page is provided for informational purposes only and does not constitute legal advice. Payment processing fees and settlement times vary by processor and are subject to change. Consult your payment processor or legal counsel for guidance specific to your business.

Built on infrastructure you already trust

StripePayment infrastructure
XeroAccounting
QuickBooks OnlineAccounting
Your own Stripe account — funds settle directly to you
Works with Xero and QuickBooks Online
No platform percentage on payments
30-day free trial, no credit card required

What businesses say about Win!

"We switched from QBO Payments and saved more on ACH fees in the first month than Win! cost us. The autopay enrollment alone cut our AR follow-up by 80%."

— Owner, Commercial HVAC contractor

"My accountant was nervous at first. After seeing that Xero reconciliation happened in real time — not end of month — she was sold. Now she recommends it to other clients."

— Director, Managed IT / MSP

"The field tech app is what got us. Techs invoice on-site, customers pay before they leave. We used to wait 45 days for service calls. Now most pay the same day."

— Operations Manager, Electrical Contractor