AI-native automation
Automate work across
Calendly and 
Mondaywith Caddi AI Agents.
Automate anything you do across Calendly, Monday, 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 Monday
Connect Calendly to Caddi
Allow1Sign in to Calendly
One click with your own Calendly login. No API keys.
Connect Monday to Caddi
Allow2Sign in to Monday
The same click again. Both tools are connected.
Create item in Monday 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 Monday together
- 01
Create item in Monday when new event scheduled in Calendly.
Caddi watches Calendly for new event scheduled and create item in Monday. No copy-paste, no missed records.
- 02
Create one-off meeting in Calendly when new item in Monday.
Caddi watches Monday for new item and create one-off meeting in Calendly so the two systems stay in lockstep.
- 03
Update item in Monday from Calendly events.
When event cancelled happens in Calendly, Caddi update item in Monday with the right context attached.
Actions Caddi can take across Calendly and Monday
- 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.
- Monday
New item
Triggers when a new item is added to a board.
- Monday
Item updated
Triggers when an item's columns change.
- Monday
Status changed
Triggers when an item's status moves to a new value.
- Monday
Create item
Add a new item to a board with column values.
- Monday
Update item
Modify column values on an existing item.
- Monday
Move item to group
Move an item between groups within a board.
Common questions
How does Caddi connect Calendly and Monday?
Calendly and Monday 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 Monday 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 Monday to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Calendly + Monday 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 Monday?
Drop your work email and we'll show you Caddi running end-to-end against Calendly, Monday, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.