Comparison
Billings Pro alternative: Invoicewell vs Billings Pro
Billings Pro is a long-running native Mac app for time and invoices, from $5 a month. Invoicewell is a new native Mac app, $19.99 once.
Invoicewell vs Billings Pro at a glance
| Feature |  |  |
|---|---|---|
| Price | $19.99 once | Free (1 invoice); Freelance $5; Professional $10 a month or $99 a year, per user |
| Invoices you can make | Unlimited | Free: 1. Freelance: 5. Professional: no limit listed |
| Native Mac app | Yes | Yes |
| iPhone, iPad, Apple Watch | No | Yes (the iPhone app was last updated October 21, 2019) |
| Works offline | Yes (email and AI need the internet) | Yes, says Marketcircle |
| Time tracking | Timer in the app and the menu bar | Yes |
| Invoices and quotes | Yes | Invoices and estimates |
| Client statements | No | Yes |
| Recurring invoices, reminders, late fees | Yes | Not covered here |
| Latest Mac version | 1.0.1, November 1, 2026 | 1.8.0, March 12, 2026 |
| Needs | macOS 14+ | macOS 12.4 or later |
| AI assistants | Claude, Cursor, Claude Code and other MCP assistants make and change drafts | Not advertised on its pages |
| Free trial | No: a live demo on this page | 30 days |
Billings Pro facts are from Marketcircle’s Billings Pro page, its pricing and its App Store listings, checked November 8, 2026. “Not covered here” means we didn’t find it on those pages, not that Billings Pro lacks it.
What Billings Pro is, and why it has fans
Billings Pro, by Marketcircle (the makers of Daylite), is one of the longest-running invoice apps on the Mac. It’s a real native app, with versions for iPhone, iPad and Apple Watch, built around tracking time and turning it into estimates, invoices and statements. Marketcircle says you can keep working without an internet connection.
It’s still sold and still runs on today’s Macs: version 1.8.0 arrived on March 12, 2026 with macOS 26 support, after a long gap since 2020.
Where Billings Pro is better
- On your wrist and your phone. Track time on iPhone, iPad and Apple Watch. Invoicewell is Mac only.
- Client statements, showing a client everything they owe in one document.
- A free plan for one invoice, one estimate and one statement, and a 30 days trial.
- Years of history. If your clients and invoices are already there, staying is simplest.
Where Invoicewell is better
- Pay once. $19.99, every feature, no invoice limits, free updates. Billings Pro is $5 or $10 a month per user.
- Made for today’s Mac. SwiftUI, ⌘K Quick Open, Touch ID lock, Quick Look and a menu bar timer, on macOS 14 Sonoma or later.
- Ask for an invoice. Claude and other AI assistants make drafts in Invoicewell, asking only what’s missing. Only you press Send.
- Getting paid. Part payments, three reminder levels and late fees, plus recurring invoices that catch up if your Mac was off.
- Clients abroad. Invoices and emails in English, Spanish, French, German, Dutch, Italian, and any currency per client.
According to Invoicewell’s own tests, with 5,000 invoices in the list, ⌘K found the one you typed in under half a second, and 328 automated tests and 602 in-app checks passed on the release build of version 1.0.1.
Try Invoicewell right here. This is a working model of the app, not a video: pick a request and answer its questions.
An example with made-up clients. The questions are the ones Invoicewell really asks.
Switching from Billings Pro to Invoicewell
Keep your records
Save PDFs of the invoices you’ve sent from Billings Pro, for your records.
Bring your clients
If you have your clients as a CSV file, import them in Invoicewell, which recognizes the usual headings and marks duplicates.
Carry on your numbers
In Settings › Numbering, set the next invoice number to follow your last Billings Pro one.
Track time the same way
Start the timer from the menu bar, then add unbilled hours to an invoice.
Which should you pick?
If you track time on an Apple Watch or iPhone, or rely on client statements, Billings Pro still does that, and its Mac app is up to date for macOS 26.
If you work at your Mac and want to stop paying monthly, Invoicewell is the native alternative: $19.99 once, no invoice limits, and Claude to do the typing.
Questions about Invoicewell and Billings Pro
Is Billings Pro still being updated?
Yes, on the Mac: version 1.8.0 came out on March 12, 2026 for macOS 26, its first update since 2020. The Billings Pro iPhone app was last updated on October 21, 2019, according to the App Store.
How much does Billings Pro cost?
Marketcircle lists a free plan (1 invoice, 1 estimate and 1 statement), Freelance at $5 per user a month (5 invoices, 5 estimates, 5 statements), and Professional at $10 per user a month or $99 a year. The Mac App Store listing says paid plans are bought in the Billings Pro iPhone app.
Is Invoicewell a good Billings Pro alternative?
Yes, if you want a native Mac app without a subscription: invoices, quotes, credit notes, recurring invoices, a menu bar timer, reminders and late fees, for $19.99 once with no invoice limit. If you need Apple Watch or iPhone apps, Billings Pro has them and Invoicewell doesn’t.
Do both work offline?
Yes. Marketcircle says Billings Pro is a native app you can keep using without an internet connection, and Invoicewell keeps everything on your Mac. Both need the internet for email, and Invoicewell’s AI assistants need it too.
Which Macs does each support?
Billings Pro 1.8.0 needs macOS 12.4 or later, per the Mac App Store. Invoicewell needs macOS 14 Sonoma or later, on Apple silicon and Intel Macs.
Can I make invoices with Claude in Billings Pro?
Not that Marketcircle’s pages say. Invoicewell connects to Claude in one click, so you can ask for an invoice in plain words and check it before you send it. See how to make invoices with Claude.
