Win back cancelled Cal.com bookings with a recovery email

By General Input

When someone cancels a Cal.com meeting, an agent sends a personalized rebook email and updates HubSpot so the lead does not slip through the cracks.

Integrations

  • Cal.com
  • Apollo
  • Gmail
  • HubSpot

Type

Agentic Task

Categories

  • Sales
  • Customer Support

Build me an agent workflow that runs every time a Cal.com booking is cancelled. The trigger should be a Cal.com poll on the booking_cancelled event.

When a cancellation comes in, the agent should:

1. Use Cal.com Get a Booking to pull the full booking details, including the cancellation reason, the attendee email and name, and the original event type (for example 'Sales intro call' or 'Customer success check-in').

2. Check the cancellation reason. If it contains phrases like 'no longer interested', 'not interested', 'wrong person', 'wrong contact', 'unsubscribe', or 'do not contact', stop here and do nothing else. Otherwise continue.

3. Call Apollo People Enrichment on the attendee's email to confirm their job title, seniority, and company. Use this only to set the right tone in the email (more formal for senior buyers, more casual for individual contributors). If Apollo returns nothing, fall back to whatever name and company Cal.com gave us.

4. Draft a short, personal recovery email in Gmail. The email should: acknowledge the cancellation by name, briefly reference the event type they had booked (without sounding scripted), and offer two clear paths. Path one is a one-click rebook link to the same Cal.com event type. Path two is a no-pressure reply option, something like 'if priorities have shifted, just reply and let me know what would be useful instead'. Keep it under 120 words. No marketing speak. Send the email via Gmail Send a Message from the host's inbox, with the original host on the From line.

5. Find the matching contact in HubSpot using Search Contacts by email. If found, update the contact with HubSpot Update Contact: set lifecycle stage to 'opportunity' if the original event type was a sales call, or 'customer at risk' if it was a customer success call. Also note the cancellation reason on the contact (in a 'last_cancellation_reason' or notes property if available).

6. Create a HubSpot Task with Create Task assigned to the deal owner on that contact, due in 3 days, titled 'Follow up: [attendee name] cancelled [event type] - check if rebooked'. Associate the task with the contact (and the deal if there is one).

If the contact is not found in HubSpot, skip the CRM update and the task and just send the recovery email.

Log a one-line summary at the end: who cancelled, which event type, whether an email was sent, and what HubSpot changes were made.

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