AI-native automation
Automate work across
Docusign 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 Docusign and Microsoft 365. Caddi builds the loop and runs it.
See it on your stack
See Caddi run Docusign 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 Docusign and Microsoft 365 together
- 01
Send email in Microsoft 365 when envelope completed in Docusign.
Caddi watches Docusign for envelope completed and send email in Microsoft 365 — no copy-paste, no missed records.
- 02
Send envelope from template in Docusign when new email in outlook in Microsoft 365.
Caddi watches Microsoft 365 for new email in outlook and send envelope from template in Docusign so the two systems stay in lockstep.
- 03
Create event in Microsoft 365 from Docusign events.
When envelope sent happens in Docusign, Caddi create event in Microsoft 365 with the right context attached.
Actions Caddi can take across Docusign and Microsoft 365
- Docusign
Envelope completed
Triggers when all signers complete an envelope.
- Docusign
Envelope sent
Triggers when an envelope is sent for signature.
- Docusign
Recipient signed
Triggers when a single recipient completes signing.
- Docusign
Envelope declined
Triggers when a recipient declines an envelope.
- Docusign
Send envelope from template
Send a pre-built template out for signature with merged fields.
- Docusign
Send envelope from document
Send an arbitrary document out for signature.
- Docusign
Void envelope
Cancel an in-flight envelope with a reason.
- Docusign
Download signed PDF
Pull the executed PDF and certificate from a completed envelope.
- Docusign
Move envelope
Move a completed envelope to a specified folder.
- 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 Docusign and Microsoft 365?
Docusign 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 Docusign 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 Docusign and Microsoft 365 to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Docusign + 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 Docusign and Microsoft 365?
Drop your work email and we'll show you Caddi running end-to-end against Docusign, Microsoft 365, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.