AI-native automation
Automate work across
Jira and 
Squarewith Caddi AI Agents.
Connect Jira and Square: Create invoice in Square when new issue in Jira. 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 Jira and Square
Caddi AI Agents find the repetitive handoffs between Jira 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 Jira and Square together
- 01
Create invoice in Square when new issue in Jira.
Caddi watches Jira for new issue and create invoice in Square. No copy-paste, no missed records.
- 02
Create issue in Jira when new payment in Square.
Caddi watches Square for new payment and create issue in Jira so the two systems stay in lockstep.
- 03
Create customer in Square from Jira events.
When issue updated happens in Jira, Caddi create customer in Square with the right context attached.
Actions Caddi can take across Jira and Square
- Jira
New issue
Triggers when a new issue is created.
- Jira
Issue updated
Triggers when an issue is modified.
- Jira
Issue transitioned
Triggers when an issue moves to a new status.
- Jira
Create issue
Add a new Jira issue with assignee, priority, and labels.
- Jira
Update issue
Modify fields on an existing issue.
- Jira
Add comment
Post a comment on an issue.
- Jira
Transition issue
Move an issue to a different workflow status.
- 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 Jira and Square?
Jira 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 Jira 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 Jira and Square to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Jira + 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 Jira and Square?
Drop your work email and we'll show you Caddi running end-to-end against Jira, Square, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.