AI-native automation
Automate work across
Square and 
Trellowith Caddi AI Agents.
Connect Square and Trello: Create card in Trello 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 Trello
Caddi AI Agents find the repetitive handoffs between Square and Trello, 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 Trello together
- 01
Create card in Trello when new payment in Square.
Caddi watches Square for new payment and create card in Trello. No copy-paste, no missed records.
- 02
Create invoice in Square when new card in Trello.
Caddi watches Trello for new card and create invoice in Square so the two systems stay in lockstep.
- 03
Move card in Trello from Square events.
When invoice paid happens in Square, Caddi move card in Trello with the right context attached.
Actions Caddi can take across Square and Trello
- 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.
- Trello
New card
Triggers when a new card is added to a list.
- Trello
Card moved
Triggers when a card is moved to a different list.
- Trello
Card archived
Triggers when a card is archived.
- Trello
Create card
Add a new card to a list with description and members.
- Trello
Move card
Move a card between lists or boards.
- Trello
Add comment
Post a comment on a card.
- Trello
Add attachment
Attach a file or URL to a card.
Common questions
How does Caddi connect Square and Trello?
Square and Trello 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 Trello 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 Trello to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Square + Trello 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 Trello?
Drop your work email and we'll show you Caddi running end-to-end against Square, Trello, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.