AI-native automation
Automate work across
Expensify and 
Microsoft Outlookby AI screensharing.
Pick any amount of tools and Caddi automates them end-to-end. No workflow builder, just show Caddi.
See it on your stack
See Caddi run Expensify and Microsoft Outlook 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.
- Screenshare to set up, chat to improve. Show Caddi once on a screenshare. Tweak it later by chat — 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 screenshare it once. The loop ships.
- 03Improve
Caddi flags upgrades to existing loops and new automations to deploy.
Practical ways to use Expensify and Microsoft Outlook together
- 01
Send email in Microsoft Outlook when new expense report in Expensify.
Caddi watches Expensify for new expense report and send email in Microsoft Outlook — no copy-paste, no missed records.
- 02
Create expense in Expensify when new email in Microsoft Outlook.
Caddi watches Microsoft Outlook for new email and create expense in Expensify so the two systems stay in lockstep.
- 03
Reply to email in Microsoft Outlook from Expensify events.
When report approved happens in Expensify, Caddi reply to email in Microsoft Outlook with the right context attached.
Actions Caddi can take across Expensify and Microsoft Outlook
- 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.
- Microsoft Outlook
New email
Triggers when a new email arrives in your inbox.
- Microsoft Outlook
New event
Triggers when a new event is added to your calendar.
- Microsoft Outlook
Flag set on email
Triggers when you flag a message for follow-up.
- Microsoft Outlook
Send email
Send a new email from your Outlook account.
- Microsoft Outlook
Reply to email
Reply to an existing email thread.
- Microsoft Outlook
Forward email
Forward an existing email to one or more recipients.
- Microsoft Outlook
Create event
Add a new calendar event with attendees and reminders.
- Microsoft Outlook
Move message
Move an email between folders.
Common questions
How does Caddi connect Expensify and Microsoft Outlook?
Expensify and Microsoft Outlook just run together. All it takes is showing us how you use them — one screenshare, no workflow builder to wire up. Caddi turns the demo into a verified loop and runs it against Expensify and Microsoft Outlook end-to-end.
Do I need engineering help?
No. Whoever does the work today shows it once on a call. 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, but once the loop ships it runs deterministically — no model in the loop at runtime.
Can Caddi connect Expensify and Microsoft Outlook to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Expensify + Microsoft Outlook 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 the screenshare. The Caddi team reviews every loop before it runs in production.
Ready to automate Expensify and Microsoft Outlook?
Drop your work email and we'll show you Caddi running end-to-end against Expensify, Microsoft Outlook, and the rest of your stack.