You can cut most manual entry in Xero by combining four tools. Wispr Flow lets you speak instead of type, JAX acts on your instructions inside Xero, Xero Documents reads and matches your bills, and SimpleAI Books prepares coded bill entries for you to approve. You review everything before it posts.
We covered these tools in a live demo at our Smarter Business Bootcamp on 16 October 2026. When we asked attendees where most of their typing time goes, keying in bills was the answer we heard most. This article walks through each tool, when to use it, and where it falls short.
The Smarter Business Bootcamp (SBB) is 361DC’s learning programme for our customers, and covers a diverse range of topics, from accounting to marketing and even the latest AI technology! Sessions are short and intense, yet practical at the same time. We have covered topics like AI tools, smart processes that cut costs, cybersecurity, Singapore business topics such as CPF, tax, InvoiceNow and more.
Where does the typing time go in Xero?
Manual work in Xero usually falls into three buckets:
- Creating and asking: creating contact details, invoice details, asking questions such as “what is my P&L this month?”, “who owes me the most money?”
- Keying in bills: creating the supplier, date, amount and tax from bills and receipts.
- Correcting mistakes: typos, wrong accounts and wrong tax codes that might only surface at month-end or year-end.
The third bucket costs more than it looks for GST-registered businesses. Singapore’s GST rate is 9% and IRAS expects you to keep tax invoices and supporting records for at least five years. A wrong tax code on a recurring supplier bill repeats every month until someone spots it. Fewer keystrokes means fewer places for that to happen.
The four tools at a glance
| Tool | What it does | Best for | Limits to know |
|---|---|---|---|
| Wispr Flow | Voice dictation. Speaks into any app where your cursor is. | Instructing JAX, writing emails, replacing typing | Dictates only, does not translate. Free plan has a weekly word limit. Audio is processed in the cloud. |
| JAX (Just Ask Xero) | Xero's AI assistant. Answers questions about your data and creates contacts, invoices and quotes. | Quick questions, contact creation and sales entries, even on the go | Unable to create bills or inventory as at time of writing. |
| Xero Documents | Replaces Files and the inbox. Reads uploaded bills, extracts line items, matches to existing transactions. | Bills you already recorded, such as repeating bills | Does not fill in the account. You still choose it. |
| SimpleAI Books | Third-party app. Reads bills and statements, suggests the account and tax code, follows custom prompts. | Bulk bill entry with consistent coding | Add-on to Xero. |
Three ways to cut manual entry in Xero
The tools combine into three workflows. Pick the one that matches the task in front of you.
Workflow 1: Speak to JAX instead of typing
This suits sales entries and quick questions, especially when you are out meeting clients. It is generally faster to speak than to type, so the time saved adds up across a day of instructions and questions.
- Set up Wispr Flow. Download it for Mac, Windows, iPhone or Android, sign up and allow microphone access.
- Open JAX in Xero. Click the JAX icon at the top right of your screen.
- Hold the Wispr Flow shortcut and speak. For example: “Show me a list of overdue invoices.” Then refine it: “Sort by amount.”
- Ask JAX to create. It can create a contact, then an invoice for that contact. If it is unsure, it asks. In our demo, it checked whether we wanted one invoice with two lines or two separate invoices, and asked for a unit price as it was not provided.
- Read the result before you confirm. The invoice’s History and Notes in Xero shows it was created through JAX.
Two Wispr Flow settings are worth changing early. Add your frequently used languages, so mixed English and Mandarin sentences are captured correctly. Then teach it your vocabulary, for example so that “zero” is written as “Xero” and “Pte Ltd” appears in short form. It also strips out filler sounds, so the text that appears reads cleanly.
Know the limits. Wispr Flow is a dictation tool, not a translator. If you speak Tamil or Chinese, it types Tamil or Chinese. JAX is improving quickly, but at the time of our session it could not create bills. Speak clearly and check the text before you send it.
Workflow 2: Upload bills to Xero Documents
Xero Documents replaced Files and the old inbox, and you will find it under Accounting. It is the lowest-effort option because it is already inside your Xero.
- In Xero, go to Accounting > Documents and go to settings on the right. Turn on automate matching transactions.
- Upload or email your bills. Drag and drop works.
- Check the matches. Documents compares each upload with transactions already in Xero and attaches it when it finds a match.
- Review the rest. Check the contact, reference and line items, choose the account, then create the transaction.
Here is a practical example. We uploaded seven documents, and four were automatically matched to bills that already existed, such as a monthly rental set up as a repeating bill. The remaining three stayed in the inbox for review. You do not re-key anything, and the right attachment lands on the right transaction. So yes, you should still set up repeating bills. Documents attaches the supplier’s actual invoice when it arrives.
Documents also reads line by line (description, quantity and price), writes a short file summary, and can read handwritten bills. If a bill has ten lines and you want only one, use Collapse line items. The gap is the account: you still choose it yourself.
Workflow 3: Let SimpleAI Books prepare the entry
SimpleAI Books is a third-party app connected to Xero. It reads bills and statements and prepares the entry, including the account. That is the part Documents leaves to you.
- Upload and process your bills in SimpleAI Books.
- Look for the exclamation mark. It flags items that need review, such as handwritten bills where the extracted text does not match.
- Check the account, tax amount and total against the supplier’s invoice.
- Approve. The bill is then created in Xero.
The strongest feature is the custom prompt. You write an instruction in plain language, test it on your recent documents, and it applies to future bills. We demonstrated three:
- Splitting a cost by department: 40% to admin and 30% each to sales and training.
- Assigning an account to certain purchases, so a given type of expense always goes to the account you choose.
- Changing the tax rate on specific lines of a phone bill, such as charges you treat as zero-rated, instead of editing each bill by hand.
It can also translate. If a supplier bill arrives in Chinese, SimpleAI Books can present it in English.
A caution on rules. A prompt applies your rule every time, including a wrong one. Confirm the GST treatment with your accountant or IRAS guidance before turning it into a rule.
Which tool should you start with?
- Mostly sales invoices and questions: start with Wispr Flow and JAX.
- Mostly recurring supplier bills: start with Xero Documents and auto-match.
- High bill volume that needs consistent coding: consider SimpleAI Books with custom prompts.
They are not either/or. Many businesses will use a mix of them.
Mistakes to avoid
- Approving without checking. AI drafts, a person verifies the account, tax code and amount. Every time.
- Rolling out to everyone at once. Pilot with one supplier or one client, fix the rules, then widen.
- Skipping the privacy terms. Read each app’s access and data terms before connecting it to Xero. Wispr Flow processes dictation in the cloud, so avoid dictating confidential details until you have checked its settings. If your documents contain personal data, review your obligations under Singapore’s PDPA.
- Entering the same thing twice. Capture once and let it flow through, rather than building it in a spreadsheet and retyping it into Xero.
Want help setting this up?
If you would like to cut data entry while working with Xero, we can walk through your current workflow and show you which tools fit. Call us at 6515 7906 or email enquiry@361dc.com. A short review usually shows where the repeated typing is, and that tells you where to start.
Free trial of SimpleAI Books: if bill entry is your biggest time cost, contact us to arrange a free trial of SimpleAI Books and test it on your own supplier bills.
If you had missed out on our Smarter Business Bootcamp (SBB) and would like to join, do also contact us for a trial.
Frequently Asked Questions
JAX (Just Ask Xero) is Xero's built-in AI assistant. You can ask about invoices, bills and payments, request insights, ask how-to questions, and create routine items such as contacts, quotes and invoices.
Not at the time of this article. It could create invoices but not bills. Features change quickly, so check Xero's current release notes.
Yes, repeating is still useful especially for fixed and recurring expenses. Create the repeating bill as usual. When the supplier's invoice arrives, upload it to Documents and auto-match attaches it to the existing bill.
Both read bills and extract details. Documents adds a file summary and auto-match to existing transactions. SimpleAI Books suggests the account and you can further enhance by using custom prompts.
No. It types what you say in the language you speak. For translating bills, SimpleAI Books can help.
It is safe when a person reviews each entry before it is approved. Start with one supplier, check the results, then expand.
