finance
Retainer billing on rails
Recurring retainer invoices sent on the same day every cycle, and late ones chased on a polite ladder, all in your voice.
How she runs it
- 1 Tell her the retainer terms once: billing day, amount, and what a renewal means.
- 2 She sends each invoice on the same day every cycle, with no missed anniversaries.
- 3 A late retainer climbs your reminder ladder automatically, written in your voice.
- 4 Replies land in your shared inbox, and anything about price or scope comes to you as one question.
Twenty-two clients on retainer means twenty-two different billing dates, unless you deliberately choose otherwise. Amber holds one schedule per client and never confuses a signup date with a billing date, so the invoice fires on the same day every cycle, prorated correctly the first time and handled the same way every month after that.
When a client goes quiet on a retainer that already fired, she runs the reminder ladder you set up at the start: a friendly nudge first, a direct ask with the invoice and amount restated, and a firmer message that waits for your yes before it goes. She sends and reminds only. Payment still runs through whatever processor you already use; she is not touching a card.
Replies land in your shared inbox, and the moment one needs a real decision, a price change, a paused month, a client asking to cancel, it becomes one question for you instead of a thread she has to guess at.
The recurring invoice setup covers the five decisions that keep a retainer book from drifting, and the chasing guide covers the ladder itself. This page is the part where running both stops being your Tuesday night.
Fair questions
Does she send retainer invoices without me checking first?
No. You approve the billing day, amount, and reminder ladder once at setup, and she runs that same schedule every cycle after that.
What happens when a client wants to change their retainer?
That is a decision, not a chase, so it comes to you. She flags the reply and waits for your call before anything about the terms changes.
Can she process payment or store a card?
No. She sends invoices and reminders only. Payment still runs through whatever processor you already use.
What if a billing date lands on a weekend or a short month?
She holds one billing day per client and handles the calendar edge cases, so a 31st-of-the-month signup or a short February does not break the schedule.