Let Rosie book appointments for you directly into your Calendly Account—no double bookings, no back-and-forth, and no missed leads. When a caller wants to schedule, Rosie will find an available time, confirm it with the caller, and create the event automatically in your calendar.
*Requires a paid Calendly account and is available on the Rosie Scale Plan or higher
How It Works
When a caller asks to book an appointment, Rosie will:
Use availability rules configured in your selected Calendly event
Offer 2–3 appointment time options to the caller
Collect any required intake responses
Create the appointment in Calendly
Calendly will send its standard confirmation email to attendees—Rosie does not send a separate confirmation text.
Choosing Your Calendly Event
After connecting Calendly, you will select which existing Calendly Event Type Rosie should use for booking (setup in Appointment Settings).
Rosie will automatically:
Use the availability schedule configured in that event
Respect any buffers, minimum notice, max future window, and rules already set in Calendly
Use the default duration defined in that event type
You can change the selected event at any time by editing your Appointment settings inside Rosie Admin.
Information Rosie Collects from Callers
Rosie pulls in the form fields* associated with your selected Calendly event and will ask callers those questions during the conversation.
Rosie will request:
First & Last Name (required)
Email (required)
Calendly event invitee form questions
*We can only sync free-form, text input questions (types: one line & multiple lines).
All other questions type are incompatible with direct scheduling via Rosie. If you have Invitee Form questions that are of another type, you'll either need to change that question to free form, delete it, or setup a new event type to use with Rosie.
Additional custom questions configured in Rosie Admin (optional)
Responses from Calendly’s intake fields are synced into the appointment in Calendly and display on the Rosie call details page.
Responses to Rosie-only custom questions are only shown in the Rosie call details page.
Connecting Calendly
Log into Rosie Admin
Go to Integrations → Calendly
Click Connect
Sign in to Calendly and authorize access
Go to Agent Settings -> Appointments
Select the Calendly Event Type Rosie should use
Toggle on Schedule Directly
Publish changes
Setup takes under a minute.
Re-syncing Your Calendar
If you change important settings in Calendly—like add new event types or change availability settings on an event type—just click Resync Calendly inside Rosie Admin so we can pull your updated configuration.
Using Appointment Links vs Direct Scheduling
You can choose to use appointment links or direct scheduling—but not both at the same time.
Pro-tip: Make sure you check your Text-a-link Departments as well. Delete any that offer to send a link to book an appointment.
FAQs
I have a Free Calendly account. Can I use this functionality?
No. Direct scheduling is only available with a paid Calendly account. (Their rules, not ours! 😉)
Will Rosie ask the same intake questions that appear on my Calendly booking link?
Yes and no. We automatically sync compatible Invitee Form questions from your Calendly account. We only support question types that are free-form (one line or multi-line). Question types like checkboxes, or multiple choice are not supported.
Do custom questions I add in Rosie get pushed into Calendly?
No. Custom questions configured in Rosie are used only during the call.
They do not get passed back into Calendly or to the calendar connected with Calendly. You’ll see those answers in the Rosie Call Details section.
Can Rosie reschedule or cancel appointments?
Not yet, but it’s planned for a future release.
Does Rosie look up previous appointment history?
Not yet, but let us know if you want this!
Rosie is offering to text a link to book an appointment instead of offering to book it directly with the customer during the call.
Check your text-a-link scenarios and FAQs. Ensure none of them reference sending a link to book an appointment.
Can I connect multiple calendar integrations?
Not at this time.
When Rosie tries to book an appointment, she responds with "It looks like that time is no longer available." Why?
Rosie responds this way when attempting to schedule the appointment fails. This can happen for two reasons:
That appointment time is no longer available. Perhaps Rosie was on a concurrent call with another customer who booked that same slot.
Booking the appointment failed. This is most likely due to misconfigured settings. Check your invitee form field question types, double check your availability settings, etc.
Coming Soon
Future releases may include:
Appointment rescheduling / cancellation
Ability to schedule different types of appointments with different configurations
Integration with more scheduling platforms
Want something else? Let us know!
Need Help?
Contact us anytime at [email protected] or chat with us in Rosie Admin.