Reminders go out late or never
When chasing depends on remembering, the first reminder often goes out weeks after the due date, if at all.
Payment reminder software that chases invoices so you don't have to.
Most late invoices aren't refused, they're forgotten. Workspace369 sends automatic payment reminders from a ready-made template: a gentle email the day after the due date, a firmer one six days later, then a final notice.
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14-day free trial. Card required. After the trial: from $29/month. Renews automatically every month until you cancel. Cancel anytime in Settings → Billing.
See plans3 stepsgentle, firmer and final notice by default
Stopsautomatically once the invoice is paid
Every planemail reminders; SMS steps from Voyager
Each email fills in the client's name, invoice number, amount and due date, and the reminders stop as soon as the invoice is paid. Email reminders are on every plan; Voyager adds SMS steps.
Key facts
Payment reminder software at Workspace369 covers 10 areas, including escalating reminder template, invoice merge fields, paid-invoice check before each send.
The workflow runs in 4 steps, from "start from the template" to "activate and let it run".
Workspace369 starts at $29/mo for 1 seat, and the Commander plan includes 20 seats and 12× Cadet usage at $299/mo.
Additional seats cost $10 each; full pricing is public on the Workspace369 pricing page.
Payment reminder software compared
Pick by what sits around the invoice. Workspace369 fits when proposal, deposit, portal and reminders belong in one tool: reminders run on a 1, 3, 7, 14 and 30-day ladder from $29 a month on Cadet. FreshBooks Lite ($23 a month, 5 billable clients) fits light bookkeeping. QuickBooks or Xero fit if the ledger comes first, and Zoho Invoice has a free plan with reminders and usage caps.
| Tool | Entry price (list) | Reminders on entry plan | Key entry-plan limit | Trial |
|---|---|---|---|---|
| Workspace369 | $29 a month (Cadet), $23.25 billed yearly | Yes, 1, 3, 7, 14, 30-day ladder | 1 seat, unlimited projects | 14 days, card required |
| FreshBooks | $23 a month (Lite) | Yes | 5 billable clients | 30 days, no card |
| QuickBooks | $38 a month (Simple Start) | Not stated | 1 user | 30 days, card not stated |
| Zoho Invoice | Free | Yes | 2 users, 3 projects, 500 invoices a year | Not stated |
| Square | Free; Plus $49 a month per location | Mentioned, plan not stated | Payment schedules need Plus | 30 days on Plus, card not stated |
| Wave | $0 (Pro $19 a month) | Pro only | Extra users need Pro | None described |
| Xero | $27 a month (Early) | Not stated | 20 invoices and quotes | Not stated |
Prices and limits from each vendor's official pricing page, checked October 22, 2026, in USD. Prices change, so confirm before you buy. Read the full buyer's guide.
Why chasing payment by hand doesn't work
Every email is awkward to write
Finding the right tone for a first nudge versus a final notice takes time, so freelancers put it off.
Paid clients still get chased
Manual lists drift out of date, and a client who already paid receives a reminder that damages the relationship.
See the workspace your clients feel.
01
Proposals to paid invoices
Send quotes, bill milestones or retainers, and let automated reminders chase anything outstanding.
02
Every channel in one inbox
Email lands beside the client record on every plan; texts, calls and voicemail join it from Voyager, with AI call summaries from Specialist.
03
Client work, organized as projects
Tasks, files, and status for every engagement — visible to the team and, through the client portal, to the client.
04
A portal clients actually check
Clients watch progress, files, and invoices in a branded portal instead of asking your team for updates.
How automatic payment reminders work
01
Start from the template
Open Workflows, choose New workflow and pick Escalating unpaid invoice reminders under Invoices.
02
Check the emails
Each email is pre-written with the client's name, invoice number, amount and due date filled in. Change any of the wording.
03
Set the timing
The workflow starts the day after the due date, waits six days before a firmer email, then sends a final notice. Click any wait to change it.
04
Activate and let it run
It runs for every invoice that goes past due and checks the invoice before each reminder, so payment stops the sequence. Pause it any time and review each run.
What the reminders include
- Agree payment terms before work starts, so the due date in the reminder is one the client accepted.
- Run a simulated test so you see exactly what a client would receive.
- On Cadet, the reminder workflow counts toward your 3 active email automations.
Escalating reminder template
Invoice merge fields
Paid-invoice check before each send
Adjustable timed waits
Run history and logs
Simulated test runs
SMS steps (Voyager)
Payment links on every invoice
Saved payment methods
AR aging report (Specialist)
Pick the plan your work needs today.
Client records, proposals, invoices, online payments, time tracking and intake forms are on every plan. Upgrade when your work needs calls, texts or more.Cadet
$29 / month
1 seat included
- Public proposal approval & signing
- Deposit on acceptance
- Proposal-to-invoice conversion
- Billable time tracking
- Public intake forms
14-day free trial. Card required. After the trial: $29/month for Cadet. Renews automatically every month until you cancel. Cancel anytime in Settings → Billing.
Voyager
$74 / month
2 seats included
Everything in Cadet, plus
- SMS messaging
- Voice & voicemail
- Shared inbox
- Missed-call text back
- No-answer forwarding
14-day free trial. Card required. After the trial: $74/month for Voyager. Renews automatically every month until you cancel. Cancel anytime in Settings → Billing.
Specialist
$149 / month
10 seats included
Everything in Voyager, plus
- Online booking
- Expense tracking
- Payment plans
- Inventory tracking
14-day free trial. Card required. After the trial: $149/month for Specialist. Renews automatically every month until you cancel. Cancel anytime in Settings → Billing.
USD monthly billing. Compare all plans.
Free account setup & migration help
Our team sets up your workspace with you and helps move your clients and invoices from the tools you use now.
Export your data as a spreadsheet and AI Import maps the columns for you. Support can help with anything unusual.
Offer ends .
Start free trial
14 days free · card required · then $29/mo · cancel anytime
After signup, claim free setup in your workspace.
What reviewers say about Workspace369.
★★★★★
SMB ModernizationGreat tool for modernizing small businesses. Ability to leverage AI without technical background.
★★★★★
True all-in-one systemIt beautifully combined my CRM, team calendar, and billing tools so I could finally stop paying for a bunch of separate software subscriptions
★★★★★
Best app for my construction businessGreat app. This app solved all my needs! Not only did it help, but it is cheaper than other apps. I highly recommend this app if you want to start organizing and automating your business on another level. Also love the design
Quoted exactly as written, in the reviewer’s own language. This is a selection of reviews, not all of them. Reviews from our own team are left out of the selection, but the overall rating includes their ratings.
See Workspace369 on your own client work.
Start your trial and send your first proposal or invoice from your own workspace. Compare plans any time; upgrade only when your work needs more. Start free trial
14-day free trial. Card required. After the trial: from $29/month. Renews automatically every month until you cancel. Cancel anytime in Settings → Billing.
Compare plansBefore you turn reminders on
What is the best payment reminder software?
It depends on what sits around the invoice. Workspace369 fits when proposals, deposits, a portal and reminders belong in one tool, from $29 a month on Cadet. If the books are the priority, compare QuickBooks, Xero and FreshBooks.
What is payment reminder software?
Payment reminder software sends follow-ups to clients with unpaid invoices on a schedule, so you don't have to write and time each email yourself. In Workspace369 the reminders are an automation tied to your invoices: they start after the due date and stop when the invoice is paid.
Do reminders stop when the client pays?
Yes. The template checks the invoice before each reminder, and once it's paid, the reminders stop.
Which plan includes automatic payment reminders?
Email reminders work on every plan, including Cadet at $29/month, where they count toward 3 active email automations. Voyager ($74/month) allows 10 active workflows and adds SMS steps.
Can I change the wording and timing?
Yes. Every email can be edited, and each wait between reminders can be shortened or lengthened.
Can clients pay straight from the reminder?
Every invoice has a payment link clients can use without an account, and payments go through your own Stripe account.
See where Workspace369 fits into your client-work flow.
Start with the modules you need today, then turn on AI, automations, accounting, inventory, requests, and reporting as the operation grows.
14-day free trial. Card required. After the trial: from $29/month. Renews automatically every month until you cancel. Cancel anytime in Settings → Billing.
