AI-native automation
Automate work across
Microsoft 365 and 
Squarewith Caddi AI Agents.
Connect Microsoft 365 and Square: Create invoice in Square when new email in outlook in Microsoft 365. 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 Microsoft 365 and Square
Caddi AI Agents find the repetitive handoffs between Microsoft 365 and Square, 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 Microsoft 365 and Square together
- 01
Create invoice in Square when new email in outlook in Microsoft 365.
Caddi watches Microsoft 365 for new email in outlook and create invoice in Square. No copy-paste, no missed records.
- 02
Send email in Microsoft 365 when new payment in Square.
Caddi watches Square for new payment and send email in Microsoft 365 so the two systems stay in lockstep.
- 03
Create customer in Square from Microsoft 365 events.
When new calendar event happens in Microsoft 365, Caddi create customer in Square with the right context attached.
Actions Caddi can take across Microsoft 365 and Square
- Microsoft 365
New email in Outlook
Triggers when a new email arrives in Outlook.
- Microsoft 365
New calendar event
Triggers when a new event is added to a calendar.
- Microsoft 365
New file in OneDrive
Triggers when a file is added to OneDrive.
- Microsoft 365
Send email
Send a new email from your Outlook account.
- Microsoft 365
Create event
Add a new event with attendees and reminders.
- Microsoft 365
Upload file to OneDrive
Add a file to a OneDrive folder.
- Microsoft 365
Create document in Word
Create a Word document with starter content.
- 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.
Common questions
How does Caddi connect Microsoft 365 and Square?
Microsoft 365 and Square 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 Microsoft 365 and Square 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 Microsoft 365 and Square to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Microsoft 365 + Square 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 Microsoft 365 and Square?
Drop your work email and we'll show you Caddi running end-to-end against Microsoft 365, Square, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.