How to Automate Invoice Sending: 5 Tools Compared

Most freelancers spend hours every month manually sending invoices, writing follow-up emails, and awkwardly chasing late payments. All of that can be automated. Here's how — and which tools do it best.

Why Automate Invoicing?

87%

of freelancers report being paid late

45 days

average late payment delay (Xero research)

30%

faster payment with automated reminders

Manual invoicing creates four failure points:

Forgetting to send: After finishing a project, the next one starts and invoicing gets pushed back days or weeks.
Delayed follow-ups: Most freelancers wait too long to chase — or feel too awkward to follow up at all.
Inconsistent tone: Manual emails swing between too friendly (ignored) and too aggressive (damaged relationship).
Lost time: Writing individual chase emails costs 15–30 minutes per invoice. Multiply by 10 overdue invoices = 5 hours wasted.

What You Can Automate

Invoice creation

Recurring invoices auto-create monthly/quarterly. Templates pre-fill client details.

✅ Fully automatable

Delivery

Invoice sent automatically on a trigger (project completion date, recurring date, or one-click send).

✅ Fully automatable

Before-due reminders

A friendly reminder 7 days before the due date increases on-time payments significantly.

✅ Fully automatable

Payment reminders

Sequential emails that escalate in tone: friendly → firm → formal demand. Sent automatically based on days overdue.

✅ Fully automatable

Payment confirmation

Thank-you email sent automatically when payment is detected (via Stripe webhook). Marks invoice as paid.

✅ Fully automatable

5 Invoice Automation Tools Compared

Tool	Auto-send?	Auto-reminders?	Price	Best for
⭐ Chaser	✅	✅ 4-stage escalation	€20/mo	Freelancers who hate chasing
FreshBooks	✅	✅ basic	$19/mo	Bookkeeping-focused freelancers
Wave	✅	⚠️ limited	Free	Beginners, low volume
QuickBooks	✅	✅	$30/mo	Small business, accounting
Zoho Invoice	✅	✅	Free–€15/mo	Multi-feature, budget-conscious

How Chaser's 4-Stage Automation Works

Most tools send one or two reminders. Chaser's system mirrors what a professional credit controller would do — but without lifting a finger:

Stage 17 days before due dateFriendly

Gentle reminder that payment is coming up. Keeps your invoice top of mind.

Stage 2Day after due dateNudge

Polite follow-up. Acknowledges they may have just forgotten. Includes invoice link.

Stage 37 days overdueFirm

More direct. Requests specific payment date. References invoice number.

Stage 414 days overdueFormal demand

Professional formal demand. References payment terms. Usually resolves 90% of remaining cases.

All 4 stages are professionally written, multilingual (EN/NL/DE/FR), and sent automatically. You can preview and customize each email. Stop when paid — automatically.

Set up invoice automation in 2 minutes 🤖

Create an invoice, click send, and let Chaser handle everything else. 4 escalating reminders, automatic paid detection, multilingual — all on free trial.

Try Chaser Free →Generate Invoice First

Frequently Asked Questions

Can I automate invoicing for free?

Yes. Wave offers free invoicing with basic automation. Chaser offers a free trial with 3 invoices including full 4-stage automation. Zoho Invoice has a free tier. For most freelancers, even a €20/month tool pays for itself with the first recovered late payment.

Will automated reminders annoy my clients?

No — when done right. Automated reminders that are professional, politely worded, and correctly timed are preferred by clients over erratic manual chasers. The key is tone calibration: start friendly, escalate gradually only if needed.

What's the difference between auto-send and auto-reminders?

Auto-send = the initial invoice goes out automatically on a schedule. Auto-reminders = follow-up emails sent automatically after the invoice is unpaid. Both together give you full hands-off invoicing.