AI-native automation

Connect Box and Calendly with AI

Pick any two tools and Caddi runs the loop between them end-to-end — no complicated workflow builder, no IT ticket.

  • Doesn't break. Caddi reads intent, so when fields move or UIs change, your loop keeps running.
  • Screenshare to set up, chat to improve. Show Caddi once on a screenshare. Tweak it later by chat — no workflow builder to re-architect.

SOC 2 attested · Human-in-the-loop · Full audit trail · 70+ tools across legal, finance, and operations

Caddi can…
BoxProductivity
Caddi can…
CalendlyProductivity
Get a demoAverage setup: one screenshare, live the same week.

Practical ways to use Box and Calendly together

  • 01

    Create one-off meeting in Calendly when new file in folder in Box.

    Caddi watches Box for new file in folder and create one-off meeting in Calendly — no copy-paste, no missed records.

  • 02

    Upload file in Box when new event scheduled in Calendly.

    Caddi watches Calendly for new event scheduled and upload file in Box so the two systems stay in lockstep.

  • 03

    Update invitee in Calendly from Box events.

    When folder shared happens in Box, Caddi update invitee in Calendly with the right context attached.

  • Brighton Jones
  • The Planning Center
  • Beveridge & Diamond
  • Palace
  • Portner & Shure
  • Knight Law Group

One continuous loop.

  1. 01Measure

    Caddi watches how the work gets done today.

  2. 02Create

    You screenshare it once. The loop ships.

  3. 03Improve

    Caddi flags upgrades to existing loops and new automations to deploy.

Actions Caddi can take across Box and Calendly

  • Box

    New file in folder

    Triggers when a file is uploaded to a watched folder.

  • Box

    Folder shared

    Triggers when a folder collaboration is added.

  • Box

    Upload file

    Add a file to a Box folder with metadata.

  • Box

    Create folder

    Create a new folder under a parent with permissions.

  • Box

    Search files

    Find files or folders with advanced search filters.

  • Box

    Move file

    Move a file between folders.

  • 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.

Common questions

How does Caddi connect Box and Calendly?

Box and Calendly just run together. All it takes is showing us how you use them — one screenshare, no workflow builder to wire up. Caddi turns the demo into a verified loop and runs it against Box and Calendly end-to-end.

Do I need engineering help?

No. Whoever does the work today shows it once on a call. 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, but once the loop ships it runs deterministically — no model in the loop at runtime.

Can Caddi connect Box and Calendly to other tools too?

Yes. Most Caddi loops span 3–6 tools. Once the first Box + Calendly 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 the screenshare. The Caddi team reviews every loop before it runs in production.

Ready to automate Box and Calendly?

Drop your work email and we'll show you Caddi running end-to-end against Box, Calendly, and the rest of your stack.