AI-native automation
Automate work across
Monday and 
Squarewith Caddi AI Agents.
Connect Monday and Square: Create invoice in Square when new item in Monday. 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 Monday and Square
Caddi AI Agents find the repetitive handoffs between Monday 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 Monday and Square together
- 01
Create invoice in Square when new item in Monday.
Caddi watches Monday for new item and create invoice in Square. No copy-paste, no missed records.
- 02
Create item in Monday when new payment in Square.
Caddi watches Square for new payment and create item in Monday so the two systems stay in lockstep.
- 03
Create customer in Square from Monday events.
When item updated happens in Monday, Caddi create customer in Square with the right context attached.
Actions Caddi can take across Monday and Square
- Monday
New item
Triggers when a new item is added to a board.
- Monday
Item updated
Triggers when an item's columns change.
- Monday
Status changed
Triggers when an item's status moves to a new value.
- Monday
Create item
Add a new item to a board with column values.
- Monday
Update item
Modify column values on an existing item.
- Monday
Move item to group
Move an item between groups within a board.
- 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 Monday and Square?
Monday 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 Monday 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 Monday and Square to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Monday + 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 Monday and Square?
Drop your work email and we'll show you Caddi running end-to-end against Monday, Square, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.