AI-native automation
Automate work across
Calendly and 
Datadogwith Caddi AI Agents.
Automate anything you do across Calendly, Datadog, and the rest of your tools. Sign in, show or tell Caddi what you want, and it runs end to end. No workflow builder.
How to connect Calendly and Datadog
Connect Calendly to Caddi
Allow1Sign in to Calendly
One click with your own Calendly login. No API keys.
Connect Datadog to Caddi
Allow2Sign in to Datadog
The same click again. Both tools are connected.
Post event in Datadog when new event scheduled in Calendly.
ScreenshareType it3Show or tell it
Screenshare the job, or type it in chat. Change it any time.
- Running
14 done1 for review
4Watch it run
Caddi does the work and flags anything unsure for review.
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 · 150+ tools across legal, finance, and operations
Practical ways to use Calendly and Datadog together
- 01
Post event in Datadog when new event scheduled in Calendly.
Caddi watches Calendly for new event scheduled and post event in Datadog. No copy-paste, no missed records.
- 02
Create one-off meeting in Calendly when monitor alert in Datadog.
Caddi watches Datadog for monitor alert and create one-off meeting in Calendly so the two systems stay in lockstep.
- 03
Mute monitor in Datadog from Calendly events.
When event cancelled happens in Calendly, Caddi mute monitor in Datadog with the right context attached.
Actions Caddi can take across Calendly and Datadog
- 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.
- Datadog
Monitor alert
Triggers when a Datadog monitor fires.
- Datadog
Alert recovered
Triggers when a monitor returns to OK.
- Datadog
New event
Triggers when an event is posted to the stream.
- Datadog
Post event
Send an event to the Datadog stream.
- Datadog
Mute monitor
Silence a monitor for a maintenance window.
- Datadog
Fetch metrics
Pull metric values for a report.
Common questions
How does Caddi connect Calendly and Datadog?
Calendly and Datadog 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 Datadog 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 Datadog to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Calendly + Datadog 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 Datadog?
Drop your work email and we'll show you Caddi running end-to-end against Calendly, Datadog, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.