Follow-up for bookkeepers: chasing receipts with AI
Late books are usually a client problem: receipts not sent, questions not answered. AI can send a short, specific request each month, make it easy to reply from a phone, remind politely when ignored, and tell you who is still holding up the close. The reminder works because it names the item, not the whole month.
Talk through your practice with the person who builds it
A free 30-minute call. You leave knowing which part of your bookkeeper to hand to AI first, what we would build, and roughly how long it takes.
One question at a time
“Please send your receipts” gets nothing. “What was the charge at the hardware store on the 9th, and which job was it for” gets an answer.
Group the questions by client and send them as one message, not one at a time. Nobody wants a trail of emails.
Make it reply-friendly
Clients answer from their phones between jobs. A link where they can photograph the receipt and tap a category beats an email thread.
Know who is holding up the close
A list of clients with open items, sorted by how long they have waited, tells you where to call. Some clients need a phone call, not a fifth email.
When you do call, the list tells you what to say: the three items, the dates, the vendors.
Picture this
Examples of what it can look like. Illustrations, not clients.
A client with six undocumented card charges gets a message listing them, and answers three by lunchtime.
A client has ignored three requests. You get a suggestion to call her instead of sending another.
Before quarter end, every client gets a short note on what you need to close the quarter.
The rules that apply, in their own words
“unfair or deceptive acts or practices in or affecting commerce, are hereby declared unlawful.”
“header information that is materially false or materially misleading.”
Sources
- 15 U.S.C. § 7704 (CAN-SPAM Act): Rules for commercial email: honest headers, opt-out, address.
- IRS: Circular 230: The rules for people who practice before the IRS.
- SBA: stay legally compliant: The Small Business Administration’s checklist for licenses, taxes and rules.
- 15 U.S.C. § 45 (FTC Act, Section 5): The federal ban on unfair or deceptive business practices, ads included.
Talk through your practice with the person who builds it
A free 30-minute call. You leave knowing which part of your bookkeeper to hand to AI first, what we would build, and roughly how long it takes.
Questions
What if a client never responds?
The system tells you, and you decide whether to book the item as uncategorized, call, or pause the work.
Does it save a lot of time?
It cuts the back and forth. How much depends on your clients. Measure it for a few months.
Should clients get a deadline?
Yes. “By the 5th so I can close on time” gives a reason, and people respond to reasons more than to nagging.
More jobs AI can take on
What Westward builds for this
Follow up automatically: the same job in similar businesses