AI-native automation
Automate work across
Jira 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 Jira and Microsoft 365. Caddi builds the loop and runs it.
See it on your stack
See Caddi run Jira 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 Jira and Microsoft 365 together
- 01
Send email in Microsoft 365 when new issue in Jira.
Caddi watches Jira for new issue and send email in Microsoft 365 — no copy-paste, no missed records.
- 02
Create issue in Jira when new email in outlook in Microsoft 365.
Caddi watches Microsoft 365 for new email in outlook and create issue in Jira so the two systems stay in lockstep.
- 03
Create event in Microsoft 365 from Jira events.
When issue updated happens in Jira, Caddi create event in Microsoft 365 with the right context attached.
Actions Caddi can take across Jira and Microsoft 365
- 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.
- 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 Jira and Microsoft 365?
Jira 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 Jira 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 Jira and Microsoft 365 to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Jira + 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 Jira and Microsoft 365?
Drop your work email and we'll show you Caddi running end-to-end against Jira, Microsoft 365, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.