AI-native automation
Automate work across
Expensify and 
Jiraby teaching Caddi like a new hire.
Pick any number of tools and Caddi automates them end-to-end. No workflow builder. You teach it the job once, the way you'd train someone new.
Help me automate email-to-Jira in Expensify and Jira. Caddi builds the loop and runs it.
See it on your stack
See Caddi run Expensify and Jira together.
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 · 70+ tools across legal, finance, and operations
One continuous loop.
- 01Measure
Caddi watches how the work gets done today.
- 02Create
You teach it the job once. The loop ships.
- 03Improve
Caddi flags upgrades to existing loops and new automations to deploy.
Practical ways to use Expensify and Jira together
- 01
Create issue in Jira when new expense report in Expensify.
Caddi watches Expensify for new expense report and create issue in Jira — no copy-paste, no missed records.
- 02
Create expense in Expensify when new issue in Jira.
Caddi watches Jira for new issue and create expense in Expensify so the two systems stay in lockstep.
- 03
Update issue in Jira from Expensify events.
When report approved happens in Expensify, Caddi update issue in Jira with the right context attached.
Actions Caddi can take across Expensify and Jira
- Expensify
New expense report
Triggers when an expense report is submitted.
- Expensify
Report approved
Triggers when a report is approved for reimbursement.
- Expensify
Create expense
Add an expense with amount, category, and receipt.
- Expensify
Create report
Open a new expense report for an employee.
- Expensify
Submit report
Submit an expense report for approval.
- 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.
Common questions
How does Caddi connect Expensify and Jira?
Expensify and Jira 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 Expensify and Jira 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 Expensify and Jira to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Expensify + Jira 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 Expensify and Jira?
Drop your work email and we'll show you Caddi running end-to-end against Expensify, Jira, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.