AI-native automation
Automate work across
Square and 
Xerowith Caddi AI Agents.
Connect Square and Xero: Create invoice in Xero when new payment in Square. Teach Caddi the job once, the way you'd train someone new, and it runs end to end. No workflow builder.
Discover, automate and govern the work between Square and Xero
Caddi AI Agents find the repetitive handoffs between Square and Xero, learn them the way a new hire would, and run them for you, with every run on the record. No workflow builder, no code.
Discover repetitive work
across all your tools.
Train an AI agent to do the work
over a video call.
Search mailMatters / Whitmore HoldingsGovern every AI agent,
every decision.
Discover repetitive work
across all your tools.
Train an AI agent to do the work
over a video call.
Search mailMatters / Whitmore HoldingsGovern every AI agent,
every decision.
Discover repetitive work
across all your tools.
Train an AI agent to do the work
over a video call.
Search mailMatters / Whitmore HoldingsGovern every AI agent,
every decision.
What Caddi is and how it works
An AI teammate that runs your back-office loops.
- Doesn't break. Caddi reads intent, so when fields move or UIs change, your loop keeps running.
- Taught like a new hire. Walk Caddi through the work once. Tweak it later by chat, with no workflow builder to re-architect.
SOC 2 attested · Human-in-the-loop · Full audit trail · 150+ tools across legal, finance, and operations
Practical ways to use Square and Xero together
- 01
Create invoice in Xero when new payment in Square.
Caddi watches Square for new payment and create invoice in Xero. No copy-paste, no missed records.
- 02
Create invoice in Square when new invoice in Xero.
Caddi watches Xero for new invoice and create invoice in Square so the two systems stay in lockstep.
- 03
Record payment in Xero from Square events.
When invoice paid happens in Square, Caddi record payment in Xero with the right context attached.
Actions Caddi can take across Square and Xero
- Square
New payment
Triggers when a payment completes.
- Square
Invoice paid
Triggers when a Square invoice is paid.
- Square
New customer
Triggers when a customer is created.
- Square
Create invoice
Send a Square invoice to a customer.
- Square
Create customer
Add a customer with contact details.
- Square
Fetch payouts
Pull payouts and fees for reconciliation.
- Xero
New invoice
Triggers when a new invoice is created.
- Xero
Payment received
Triggers when a payment is recorded.
- Xero
New contact
Triggers when a new contact is added.
- Xero
Create invoice
Generate an invoice for a contact with line items.
- Xero
Record payment
Apply a payment against one or more invoices.
- Xero
Create contact
Add a new Xero contact.
- Xero
Create bill
Record a new bill against a vendor.
Common questions
How does Caddi connect Square and Xero?
Square and Xero just run together. You teach Caddi the way you'd teach a new hire: walk it through how you use them today, with no workflow builder to wire up. Caddi turns that walkthrough into a verified loop and runs it against Square and Xero end-to-end.
Do I need engineering help?
No. Whoever does the work today walks Caddi through it on a call, the same way they'd train a new hire. Caddi builds the loop. No code, no IT ticket.
Is my data safe?
Yes. Caddi is SOC 2 attested. The AI watches and builds the automation, and once the loop ships it runs as deterministic code, repeatable and logged, with any model step scoped and reviewable.
Can Caddi connect Square and Xero to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Square + Xero loop is live, Caddi suggests other tools and other workflows to fold in.
How fast can it go live?
Typical first loops ship within a week of that first walkthrough. The Caddi team reviews every loop before it runs in production.
Ready to automate Square and Xero?
Drop your work email and we'll show you Caddi running end-to-end against Square, Xero, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.