Find it
The money you forgot
A two-minute scan of your last 90 days of sent mail shows every invoice still unpaid, including PDFs and invoices sent from Stripe, Razorpay or Zoho.
Chase it
Without the awkward email
Reminders that sound like you (learned from emails you have sent), timed to the due date and friendly first. Send each one yourself, or let them go out on their own: each waits 24 hours so you can read, edit or stop it, and it never chases a client who's paid.
Know it
Who pays, and how slowly
What's owed, what's overdue and each client's average days to pay, in the app and in your Monday email.
How it works
What Courtside does in the background while you get on with the work.
- Your courtMon 9:00
You sign in with Google. Two minutes later: 3 unpaid invoices, $5,250 owed, including one from August you'd forgotten about.
- Their courtThu 7:00
Invoice #1042 passed its due date yesterday. A reminder is drafted in your thread with the amount and the payment link, for you to send, edit or skip:
Hi Marcus, invoice #1042 for $1,200 was due on 3 October. Could you let me know when payment will go through?
- Their courtFri 11:20
Marcus replies: "Paid this morning, sorry for the delay." Courtside marks the invoice paid and stops chasing. If a reply only says it's on its way, Courtside asks you before drafting anything firmer.
- Your courtMon 7:00
Your Monday email: $1,200 paid last week, $650 overdue, and Brightside pays in 34 days on average. Replies you owe are sorted and drafted too.
Head to head
Every AI inbox now helps you write and summarise. We haven't found one that finds your unpaid invoices and chases them. That's what Courtside is built for; the inbox help comes with it.
| Feature | Gmail AI | Outlook Copilot | AI inbox apps | Courtside |
|---|---|---|---|---|
| Finds unpaid invoices in your sent mail | ||||
| Chases unpaid invoices, timed to the due date | ||||
| Shows how fast each client pays | ||||
| Drafts follow-ups on a schedule, firmer each time | Some | |||
| Resurfaces sent emails that got no reply | Basic | Some | ||
| Works inside the Gmail you already use | Some | |||
| Reply suggestions | ||||
| Thread summaries | ||||
| AI files mail into categories you define | Basic | Some | Some | |
| Shows why each email was sorted, and remembers your fixes | Some | |||
| Warns when Reply-To would send your answer to a different domain |
AI inbox apps: Superhuman, Shortwave and Fyxer. "Some" means at least one of them does it. "Basic" is Gmail's Nudges, which resurface some unanswered mail but don't draft anything.
Price and fit
Most AI email tools help you write faster. Courtside is built to get you paid, at a price one recovered invoice covers many times over.
Gmail's AI
Inside Gmail · Free
Writing help, summaries, basic follow-up nudges
Microsoft 365 Copilot
Inside Outlook · About $30 on top of Microsoft 365
Teams already on Microsoft 365
Superhuman
Its own email app · From about $30; AI drafts on the $40 plan
Speed and keyboard flow
Shortwave
Its own app for Gmail · Paid plans
AI search and an inbox assistant
Fyxer
Inside Gmail or Outlook · From about $22 to $49
Sorting, drafts and meeting notes
Courtside
Inside Gmail · Free, or $12 for Pro
Getting paid: finds unpaid invoices and drafts the reminders
Based on public pricing and third-party comparisons, October 2026. Plans change often; check each vendor.
Your privacy
- Nothing is sent without your OK. Switch on automatic reminders and each one waits 24 hours, so you can read, edit or stop it.
- Email bodies are never stored.
- Your mail never trains AI and is never sold.
- Tracking pixels stay blocked until you allow images.
Pricing
Pro is free until it gets you paid: it stays free until an invoice you were reminding a client about is paid, then for one more week (up to 60 days in all). No card needed. After that, stay on Free or keep Pro.
Free
$0
forever
- A scan of your last 90 days for unpaid invoices
- Every invoice and question you send tracked until it's paid or answered
- Inbox sorting into Needs reply, FYI, Newsletters and more
- 20 AI reply drafts a day
- Promises you made, tracked with due dates
Pro · Get paid
$12 / month
or $120 a year, two months free
Get-paid guarantee: if no overdue invoice is paid in your first 30 days of paid Pro, ask for your first payment back in Settings.
- Everything in Free
- Reminders drafted for you, timed to each invoice's due date, with the payment link
- Follow-up autopilot: firmer each time, never to a client who's paid
- Automatic reminders if you switch them on, each held 24 hours so you can stop it
- Money report: what's owed, overdue and paid, and how fast each client pays
- 100 AI drafts a day, your own categories, client tracking
- Morning briefing email, with the week's money on Mondays
- Get-paid guarantee: no overdue invoice paid in your first 30 days, your first payment back
Prices in US dollars; checkout shows your local currency and taxes. Cancel any time. Delete everything in one click.