AI-native automation
Automate work across
Calendly and 
Jiraby 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 email-to-Jira in Calendly and Jira. Caddi builds the loop and runs it.
See it on your stack
See Caddi run Calendly and Jira 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 Calendly and Jira together
- 01
Create issue in Jira when new event scheduled in Calendly.
Caddi watches Calendly for new event scheduled and create issue in Jira — no copy-paste, no missed records.
- 02
Create one-off meeting in Calendly when new issue in Jira.
Caddi watches Jira for new issue and create one-off meeting in Calendly so the two systems stay in lockstep.
- 03
Update issue in Jira from Calendly events.
When event cancelled happens in Calendly, Caddi update issue in Jira with the right context attached.
Actions Caddi can take across Calendly and Jira
- Calendly
New event scheduled
Triggers when an invitee books a meeting.
- Calendly
Event cancelled
Triggers when a scheduled meeting is cancelled.
- Calendly
No-show recorded
Triggers when an invitee is marked as a no-show.
- Calendly
Create one-off meeting
Spin up a one-off meeting link with custom configuration.
- Calendly
Update invitee
Modify an existing invitee's details or registration.
- 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.
Common questions
How does Caddi connect Calendly and Jira?
Calendly and Jira 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 Calendly and Jira 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 Calendly and Jira to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Calendly + Jira 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 Calendly and Jira?
Drop your work email and we'll show you Caddi running end-to-end against Calendly, Jira, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.