AI-native automation
Automate work across
Adobe Sign and 
Microsoft 365by 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 new Hire Tracker Cleanup in Adobe Sign and Microsoft 365. Caddi builds the loop and runs it.
See it on your stack
See Caddi run Adobe Sign and Microsoft 365 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 Adobe Sign and Microsoft 365 together
- 01
Send email in Microsoft 365 when agreement completed in Adobe Sign.
Caddi watches Adobe Sign for agreement completed and send email in Microsoft 365 — no copy-paste, no missed records.
- 02
Send agreement for signature in Adobe Sign when new email in outlook in Microsoft 365.
Caddi watches Microsoft 365 for new email in outlook and send agreement for signature in Adobe Sign so the two systems stay in lockstep.
- 03
Create event in Microsoft 365 from Adobe Sign events.
When agreement sent happens in Adobe Sign, Caddi create event in Microsoft 365 with the right context attached.
Actions Caddi can take across Adobe Sign and Microsoft 365
- Adobe Sign
Agreement completed
Triggers when all signers have completed an agreement.
- Adobe Sign
Agreement sent
Triggers when an agreement is sent for signature.
- Adobe Sign
Agreement declined
Triggers when a signer declines an agreement.
- Adobe Sign
Send agreement for signature
Send a document or template out for e-signature.
- Adobe Sign
Use template
Send an agreement built from a reusable widget or template.
- Adobe Sign
Download signed PDF
Download the executed PDF and certificate of completion.
- Adobe Sign
Send reminder
Nudge signers who haven't completed yet.
- Microsoft 365
New email in Outlook
Triggers when a new email arrives in Outlook.
- Microsoft 365
New calendar event
Triggers when a new event is added to a calendar.
- Microsoft 365
New file in OneDrive
Triggers when a file is added to OneDrive.
- Microsoft 365
Send email
Send a new email from your Outlook account.
- Microsoft 365
Create event
Add a new event with attendees and reminders.
- Microsoft 365
Upload file to OneDrive
Add a file to a OneDrive folder.
- Microsoft 365
Create document in Word
Create a Word document with starter content.
Common questions
How does Caddi connect Adobe Sign and Microsoft 365?
Adobe Sign and Microsoft 365 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 Adobe Sign and Microsoft 365 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 Adobe Sign and Microsoft 365 to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Adobe Sign + Microsoft 365 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 Adobe Sign and Microsoft 365?
Drop your work email and we'll show you Caddi running end-to-end against Adobe Sign, Microsoft 365, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.