Every retainer invoice goes out on the same day of the month, with the right amount, the right reference, and a note covering the period, without you remembering any of it. The most predictable revenue you have should not depend on the least reliable part of your month.
The Invoice Generator is a live Taskade Genesis app you can plan a cycle in on this page. It produces the invoice itself, which is the piece you would otherwise build first; the repeating schedule is what this prompt adds around it. Try it, then click "Use this app" to clone and own a copy in about ten seconds and set the cycle dates, uplift rules, and pre-send review described below.
The build gives you one calendar holding every recurring arrangement: the client, the amount, the billing day, the period covered, the contract end date, and any scheduled uplift. The agent prepares each cycle a few days ahead so you review rather than assemble, catches the things that silently cost money, a contract that ended two months ago and is still billing, an agreed annual increase that never got applied, a client whose scope grew without the retainer moving, and drafts the renewal conversation before the contract lapses.
Workspace DNA is why the cycle improves instead of merely repeating. Memory holds every arrangement, uplift, and contract date, so nothing depends on the person who set it up still being here. Intelligence, powered by 15+ frontier models from OpenAI, Anthropic, Google, and open-weight providers, compares what you are billing against what you agreed and against what you are delivering. Execution prepares and issues the cycle on the day, every month.
The AI agents inside the app carry 34 built-in tools, and persistent memory plus custom slash commands make the monthly review quick: ask which retainers have not changed price in over a year and the answer arrives with the amounts and the dates. The agent drafts renewal and uplift conversations well before they are urgent, which is the only time those conversations go well.
Retainer revenue is the most valuable revenue a service business has, and it is also the most neglected. Contracts lapse quietly, scope grows without price, and increases go unapplied because nobody wanted to raise it that month. Making the cycle a system removes all three failure modes at once.
Run the cycle in the view that fits:
- Calendar view for the billing schedule across the month
- Table view for every retainer with amounts and billing days
- Board view to track this cycle from prepared to issued to paid
- List view for the review queue before issue day
- Plus the rest of the 7 project views
Automations issue the cycle. A scheduled Taskade automation creates each invoice on its billing day, applies the current amount, attaches the payment link, and notifies the account owner. Across 100+ bidirectional integrations, Stripe handles the charge and Gmail delivers the invoice while Slack confirms the run completed. See recurring runs and scheduled automations.
Clone it, invite whoever owns each account, and the cycle runs without a single reminder in anyone's head.
A boundary: this issues and tracks recurring invoices as an operations layer. Revenue recognition across the period is an accounting treatment your accountant handles from the same facts.
If you do one review a year, make it a scope check against price on every retainer. Scope creep on recurring work is gradual and almost never renegotiated at the time, so the gap only becomes visible when someone deliberately compares what was agreed with what is now being delivered. The app keeps both, which makes that a ten-minute exercise instead of an archaeology project.
Browse recurring billing setups in the Community Gallery, start yours at Taskade Genesis, or read invoice automation. Pair it with Track Retainer Balance and Drawdown so usage is visible, and with Run a Monthly Billing Cycle Checklist for everything else the month needs.
Frequently Asked Questions
Should I bill retainers in advance or in arrears?
In advance is standard for retainers and much better for cash flow, because you hold the money before you do the work. The app supports either and states which basis each client is on, so it never becomes ambiguous.
What if the retainer amount changes mid-contract?
Record the new amount with an effective date. Invoices before it keep the old figure and invoices after use the new one, so history stays accurate and nobody has to remember when the change happened.
Does it handle annual uplifts?
Yes. Schedule the increase with its date and the agent drafts the notice in advance, then applies it automatically. Uplifts that are agreed but never applied are one of the most common quiet revenue leaks in agency work.
What happens when a contract ends?
The app stops billing on the end date and prompts a renewal conversation before it arrives. Billing past a contract end is embarrassing and entirely avoidable.
Can each client have a different billing day?
Yes. Spreading billing days across the month smooths your cash arrivals, which is worth doing deliberately rather than having everything land on the first.
Will I get a chance to review before invoices go out?
The cycle is prepared ahead of the billing day and waits for your approval if you want it to. Larger teams often auto-issue small retainers and review the big ones.
Does it work alongside project invoices for the same client?
Yes. A client can hold a retainer and project invoices at once, and the client view shows both so the total picture is never split across two systems.
