AI-native automation
Automate work across
Calendly and 
Redtail CRMwith Caddi AI Agents.
Automate anything you do across Calendly, Redtail CRM, 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 Redtail CRM
Connect Calendly to Caddi
Allow1Sign in to Calendly
One click with your own Calendly login. No API keys.
Connect Redtail CRM to Caddi
Allow2Sign in to Redtail CRM
The same click again. Both tools are connected.
Log every Calendly intro call against the Redtail contact.
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 Redtail CRM together
At an RIA the work between Calendly and Redtail CRM is organized by household: the right client, the right accounts, the right advisor. Caddi carries that context through every step, so records stay tied to the household they belong to.
- 01
Log every Calendly intro call against the Redtail contact.
When a prospect books through Calendly, Caddi finds or creates the Redtail contact, writes the meeting as an activity, and sets the advisor's follow-up task so nothing sits in an inbox.
- 02
Brief the advisor before the meeting starts.
Ahead of each scheduled event, Caddi pulls the contact's Redtail history, recent notes, and open tasks into a short prep note, so the advisor walks in current instead of reading the file in the waiting room.
- 03
Close the loop on cancellations and no-shows.
A cancelled or no-show Calendly event updates the Redtail activity record and re-opens the follow-up task, so the prospect goes back in the queue rather than quietly disappearing.
Actions Caddi can take across Calendly and Redtail CRM
- 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 Calendly and Redtail CRM?
Calendly and Redtail CRM 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 Redtail CRM 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 Redtail CRM to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Calendly + Redtail CRM 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.
Does this work for RIAs and financial advisors?
Yes. Caddi runs Calendly and Redtail CRM with the household as the unit of work, so plans, accounts, and activity stay tied to the right client and advisor. Firms most often start with onboarding, account maintenance, or reporting prep.
Ready to automate Calendly and Redtail CRM?
Drop your work email and we'll show you Caddi running end-to-end against Calendly, Redtail CRM, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.