Below is a practical, step‑by‑step plan you can start using today to send recurring invoices and greatly increase the chance you get paid on time — plus sample wording, a reminder schedule, and implementation checklist.

1. Pick the right billing model

• Subscription / recurring-payment (automatic charge) — best when the amount is fixed each period and you want guaranteed, hands‑off collection. Use a billing tool that supports recurring payments/autopay. QuickBooks, for example, supports recurring invoices and “Autopay” so customers can be charged automatically on your schedule. (quickbooks.intuit.com)
• Recurring invoice (customer pays each time) — useful when amounts vary month‑to‑month; still automate sending and reminders but payments require customer action.

2. Use software that automates invoices, payments and reminders

• Choose a tool that: schedules recurring invoices, includes a “Pay Now” link, supports multiple payment methods (card, ACH/bank debit, PayPal), and sends automated reminders/dunning sequences. Automation cuts manual work and reduces late payments (autopay/recurring payments are designed for reliable cash flow). (quickbooks.intuit.com)

3. Make invoices frictionless to pay

• Always include a clear “Pay Now” button or link and list accepted methods (credit card, ACH, bank transfer, PayPal, etc.). More payment options = fewer reasons to delay. Offer ACH/direct debit for recurring billing when possible — ACH typically has much lower processing fees than credit cards, making it cost‑effective for recurring or high‑value invoices. (invoiced.com)

4. Be explicit and fair about terms (and keep them short)

• Put payment terms where they’re impossible to miss: top of invoice and in client contract. Use plain language: “Payment due within 15 days (Due: Sept 29, 2025)” rather than only “Net 15.” Shorter terms generally get you paid faster; many businesses now use 7–14 day windows instead of Net 30. (xero.com)

5. Use incentives + deterrents

• Early‑payment discount: e.g., “2% if paid within 10 days (2/10 Net 30).”
• Late fee / interest: e.g., “Late payment fee: 1.5% per month (18% APR) or $25, whichever is greater,” stated clearly on invoice and in contract. Automate late fees where your software supports it. FreshBooks, for example, supports automatic reminders and applying late fees. (support.freshbooks.com)

6. Set an automated reminder and dunning schedule (example)

• Day 0 (invoice date): send invoice with payment link (and mark due date clearly).
• Due −3 days: friendly reminder (optional, useful for subscriptions or recurring services).
• Due date: “Payment due today” reminder.
• Due +3 days: first past‑due reminder (polite, request confirmation of payment).
• Due +10 days: second past‑due reminder (state late fee now applies if included).
• Due +30 days: final notice before escalation (phone call, pause service, collections). Automate these emails in your billing software to remove friction.

7. Require autopay or deposits for new or high‑risk clients

• For new customers or large invoices, require a deposit (e.g., 25–50%) or set payment method on file for recurring charges. This reduces disputes and late payments.

8. Connect invoicing to your accounting and reconciliation process

• Link your billing tool to your bank/accounting system so payments auto‑match and you can track outstanding balances, aging reports, and Days Sales Outstanding (DSO).

9. Keep communication professional and personal

• When an invoice is late, call the contact — many late payments are simple oversight. Keep written records of all communications and any agreed amended terms.

10. Track metrics and iterate

• Monitor: % invoices paid on time, average DSO, number of dunning steps before payment. Use these to tighten terms, change payment methods offered, or adjust onboarding.

Sample invoice wording (use plain, visible language)

• Payment terms line: “Payment due within 15 days. Due: Sept 29, 2025.”
• Pay link line: “Pay now: [Pay with card / Bank transfer / ACH]”
• Late fee line (if you plan to apply): “Late fee: 1.5% per month (18% APR) or $25 minimum, applied 7 days after due date.”

Sample email templates

• Initial invoice (subject: Invoice #123 — Due Sept 29, 2025) Hi [Name], attached is Invoice #123 for [service]. Total: $X. Payment due within 15 days (Due: Sept 29, 2025). You can pay securely here: [Pay link]. Thanks — [Your name/company]
• Friendly reminder (3 days before due) Hi [Name], just a quick reminder that Invoice #123 for $X is due on Sept 29, 2025. Pay here: [link]. Let me know if you need anything.
• Past‑due notice (7 days after due) Hi [Name], our records show Invoice #123 is past due by 7 days. If payment has been sent, please forward confirmation. If not, please pay here: [link]. Note: a late fee of 1.5%/month applies per our terms.

Legal/contract basics

• Put terms in the signed contract or engagement letter before work begins (payment methods, frequency, late fee policy, cancellation/termination rules).
• For recurring ACH debits, get written authorization (many processors provide an authorization form or online acceptance).
• Confirm any regulatory/tax requirements with an accountant (sales tax, 1099s for contractors, etc.).

Implementation checklist (one‑page)

• Decide billing model: subscription vs recurring invoice.
• Choose a billing tool that supports autopay, payment links, and automated reminders.
• Add payment methods: card + ACH + digital wallets as appropriate.
• Decide terms (Due on receipt / Net 7 / Net 15 / Net 30) and late fee policy; add to contract and invoices.
• Create email templates and set reminder schedule.
• Test a recurring invoice and autopay flow with a friendly client or internal test customer.
• Connect to accounting and track DSO and aging.

Recommended tools (examples to evaluate)

• QuickBooks Online (recurring invoices, Autopay, accounting integration). (quickbooks.intuit.com)
• FreshBooks (automated reminders, late fees). (support.freshbooks.com)
• Stripe / GoCardless / PayPal (recurring billing/subscriptions and card/ACH options).
• Consider a dedicated ACH-enabled processor if fees matter — ACH is often much cheaper than card processing for recurring/high-value B2B invoices. (invoiced.com)

Key facts to remember (quick)

• Automation (recurring payments/autopay + reminders) reduces late payments and manual work. (quickbooks.intuit.com)
• Offer a mix of payment options and use ACH for lower processing costs when appropriate. (invoiced.com)
• Shorter terms and clear plain‑language due dates improve speed of payment. (xero.com)
• Use reminders and enforce late fees consistently — automated systems make this painless. (support.freshbooks.com)
• Put payment terms in writing (contract + invoice) to avoid disputes and to support collections if needed. (sba.gov)

If you’d like, I can:

• Draft invoice templates and email sequences customized to your business (amounts, frequency, tone).
• Recommend 2–3 invoicing tools based on your industry, volume, and desired payment methods and compare fees/features.

Which would you like me to do next?