The Calendly integration lets you connect your Calendly account to Reply and add meeting links to your sequences. When a prospect books or cancels a meeting, Reply updates the prospect automatically so you can track meeting activity.
How to connect your Calendly account?
💡Note: To use Calendly in Reply, your Calendly account must be on a paid plan or an active trial.
To connect your account:
Go to Settings → Meetings.
Log in to your Calendly account.
Click Connect Calendly account.
Once connected, Reply can receive booking events from Calendly and update the contact status to Meeting Booked.
If Create a new contact if one doesn't exist option is enabled, Reply automatically creates a contact when someone books a meeting via Calendly and the contact does not already exist in your Reply account.
You can reconnect or disconnect the Calendly account at any time. To disconnect it, click the bin icon.
💡 Note:
Reply supports only one meeting booking source at a time. You can use either Google Calendar or Calendly.
You can connect only one Calendly account to your Reply account.
How to add a Calendly link to a sequence?
After connecting Calendly, you can insert meeting links into your messages.
Open a sequence.
Add an email step.
In the editor, select Insert Calendly link.
Choose a meeting from your Calendly account and select the text that will be shown in the message.
Click Insert.
Reply supports My events and other users' personal events in Calendly. Team or shared events in Calendly are not supported.
AI reply handling
You can set up AI reply handling so meetings are booked directly from conversations between you (or Jason AI) and prospects.
How it works
If a prospect suggests a specific time → The system books the meeting, sends the invite, and updates the prospect's status to Meeting Booked.
If a prospect suggests multiple times → Reply checks your calendar and books the first available slot.
If a prospect agrees to meet but doesn't suggest a time → Jason AI suggests time slots based on your calendar. Once a time is selected, the meeting is booked automatically.
If a prospect asks to reschedule → If a new time is provided, Reply books it after checking your calendar. If no time is provided, Jason AI suggests alternative slots.
To enable it:
For non-AI SDR sequences: Go to AI Replies in your sequence.
For AI SDR sequences: Go to Jason AI → Jason AI assistant.
Select your meeting service:
Choose Calendly in the Which meeting scheduling service would you prefer to use section
Select the event type
(Optional) Enable and add follow-ups:
Send follow up once meeting is booked
Send follow up once meeting is canceled
To send follow-ups automatically:
For non-AI SDR sequences: Enable Send automatically under “What would you like to do with the AI-generated reply?”
For AI SDR sequences: Enable Send automatically under both “What would you like to do with the AI-generated reply?” and “What would you like to do with AI-generated re-engagement follow-ups?”
💡 Important: Automatic meeting booking works only with event types that use one of the following locations: Zoom, Google Meet, Microsoft Teams, Webex, or Go to Meeting.
Event types with locations such as Custom, Ask Invitee, Phone Call, or In-Person are not supported.
Please make sure your selected event type has only one location configured. If multiple locations are set, the system will use the first one in the list.
What happens when a meeting is booked or canceled?
When a prospect schedules a meeting through a Calendly link, Reply receives the booking event from Calendly and identifies the prospect by email. The prospect is then assigned the Meeting Booked status and marked as Finished, which stops any further steps in the sequence.
If the prospect does not already exist in Reply, and Create a new contact if one doesn't exist is enabled, Reply automatically adds a new contact.
When a meeting is canceled, Reply removes the Meeting Booked status and records the cancellation in the prospect's Activity card.
👉 See also: Meeting booking with Google Calendar