AI-native automation
Automate work across
Dropbox Sign and 
Microsoft Outlookby 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 claim Email Thread Triage in Dropbox Sign and Microsoft Outlook. Caddi builds the loop and runs it.
See it on your stack
See Caddi run Dropbox Sign 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.
- 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 Dropbox Sign and Microsoft Outlook together
- 01
Send email in Microsoft Outlook when signature request completed in Dropbox Sign.
Caddi watches Dropbox Sign for signature request completed and send email in Microsoft Outlook — no copy-paste, no missed records.
- 02
Send signature request in Dropbox Sign when new email in Microsoft Outlook.
Caddi watches Microsoft Outlook for new email and send signature request in Dropbox Sign so the two systems stay in lockstep.
- 03
Reply to email in Microsoft Outlook from Dropbox Sign events.
When signature request sent happens in Dropbox Sign, Caddi reply to email in Microsoft Outlook with the right context attached.
Actions Caddi can take across Dropbox Sign and Microsoft Outlook
- Dropbox Sign
Signature request completed
Triggers when all signers complete a request.
- Dropbox Sign
Signature request sent
Triggers when a request is sent for signature.
- Dropbox Sign
Signer declined
Triggers when a signer declines a request.
- Dropbox Sign
Send signature request
Send a document or template for e-signature.
- Dropbox Sign
Use template
Send a request built from a reusable template.
- Dropbox Sign
Download signed PDF
Pull the executed PDF and audit trail.
- Dropbox Sign
Send reminder
Nudge signers who haven't completed.
- 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 Dropbox Sign and Microsoft Outlook?
Dropbox Sign and Microsoft Outlook 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 Dropbox Sign and Microsoft Outlook 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 Dropbox Sign and Microsoft Outlook to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Dropbox Sign + 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 that first walkthrough. The Caddi team reviews every loop before it runs in production.
Ready to automate Dropbox Sign and Microsoft Outlook?
Drop your work email and we'll show you Caddi running end-to-end against Dropbox Sign, Microsoft Outlook, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.