Integrations

Calendly Integration

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Overview

The Calendly integration enables your AI assistant to handle meeting scheduling automatically, from availability checking to booking confirmation. This hands-off approach eliminates back-and-forth coordination and ensures accurate, timezone-aware scheduling.

Key Benefits

Automated Scheduling
Your AI assistant manages the entire scheduling process from start to finish. Callers can book appointments directly during conversations without any manual intervention, reducing administrative overhead and improving customer experience.

Real-Time Availability
Gail checks your Calendly availability in real-time and only offers times that work with your schedule. This prevents double-bookings and ensures that appointments are scheduled during your configured availability windows.

Timezone Intelligence
The integration automatically detects the caller’s timezone and converts times appropriately. This prevents common scheduling mistakes caused by timezone confusion and ensures both parties see the meeting time in their local timezone.

Selective Event Control
Choose which Calendly event types are available for AI-assisted booking. Keep sensitive or internal meetings private while making customer-facing appointments publicly schedulable through your AI assistant.

Setup Requirements

Before you begin, ensure you have:

  • An active Gail account with admin permissions
  • A Calendly Standard plan or higher (required for Personal Access Token)
  • At least one configured event type in Calendly

Free and Essentials Calendly plans do not support Personal Access Tokens and cannot be integrated with Gail. You must have a Standard, Teams, or Enterprise plan.

Setting Up the Integration

Step 1: Generate Calendly Personal Access Token

  1. Log in to your Calendly account
  2. Navigate to Settings in the top navigation
  3. Click on Integrations in the left sidebar
  4. Select API & Webhooks
  5. In the Personal Access Tokens section, click Generate New Token
  6. Give your token a descriptive name (e.g., “Gail Integration”)
  7. Copy the generated token immediately and store it securely

Your Personal Access Token will only be displayed once. If you lose it, you’ll need to generate a new token and update your Gail integration settings.

Step 2: Connect Calendly to Gail

  1. Sign into your Gail account
  2. Navigate to Settings from the main menu
  3. Click on Integrations in the settings sidebar
  4. Find and select Calendly Integration
  5. Paste your Personal Access Token into the provided field
  6. Click Save to establish the connection

Step 3: Configure Event Types

After connecting your Calendly account, you’ll see a list of all your Calendly event types.

  1. Review the list of available event types
  2. Toggle on the event types you want to make available for AI-assisted booking
  3. Toggle off any event types that should remain private or require manual coordination
  4. Click Save Changes to apply your configuration

Example Configuration:

  • ✅ 30-Minute Consultation — Enabled for customer bookings
  • ✅ Initial Discovery Call — Enabled for prospect scheduling
  • ❌ Internal Team Sync — Disabled to prevent external booking
  • ❌ Executive Briefing — Disabled to maintain control over sensitive meetings

Only explicitly enabled event types will be available for your AI assistant to book. You can update this configuration at any time without affecting existing appointments.

How It Works

Once configured, your AI assistant manages the complete scheduling workflow during customer interactions.

Scheduling Flow

  1. Request Capture
    The caller expresses interest in scheduling a meeting, and the AI assistant begins the booking process.

  2. Availability Check
    The assistant queries Calendly in real-time to retrieve available time slots based on your configured event types and working hours.

  3. Timezone Detection
    The caller’s timezone is automatically detected based on their phone number or location. If uncertain, the assistant confirms the timezone verbally.

  4. Time Presentation
    Available times are presented to the caller in their local timezone with clear timezone labels to prevent confusion.

  5. Timezone Conversion
    If the caller is in a different timezone, the assistant automatically converts and explains times in both timezones to ensure clarity.

  6. Confirmation
    Before booking, the assistant confirms all details including:

    • Meeting date and time
    • Timezone
    • Meeting type (event name)
    • Caller’s name and email address
    • Meeting duration

  7. Booking
    Once confirmed, the appointment is booked directly through the Calendly API and appears immediately on your Calendly calendar.

Timezone Handling

Timezone accuracy is critical for successful scheduling. The Calendly integration handles this automatically:

  • Automatic Detection: The system detects the caller’s timezone based on phone number area code and location data
  • Clear Communication: Available times are always labeled with the relevant timezone
  • Dual-Timezone Display: When caller and calendar owner are in different zones, times may be presented in both timezones
  • Verbal Confirmation: The assistant confirms the timezone before finalizing the booking to catch any discrepancies

Testing Your Integration

Before using the Calendly integration with customers, verify it’s working correctly.

Step 1: Verify Connection Status

  1. In your Gail account, go to Settings → Integrations → Calendly Integration
  2. Confirm that the connection status shows as Connected
  3. Verify that your event types are listed and correctly enabled/disabled

Step 2: Test Availability Retrieval

  1. Create a test scenario where your AI assistant needs to schedule an appointment
  2. Verify that:
    • The assistant can retrieve available times
    • Offered times match your Calendly availability settings
    • Only enabled event types are presented as options

Step 3: Complete Test Booking

  1. Schedule a test appointment through your AI assistant
  2. Confirm the details during the booking process
  3. Check your Calendly dashboard to verify:
    • The appointment appears correctly
    • Date, time, and timezone are accurate
    • Attendee information is captured properly
    • The correct event type was booked

Step 4: Test Timezone Handling

  1. If possible, test with a phone number from a different timezone
  2. Verify that:
    • The timezone is detected correctly
    • Times are presented in the caller’s timezone
    • The final booking reflects the correct time in both timezones

Managing Your Integration

Updating Event Type Availability

You can change which event types are available at any time:

  1. Navigate to Settings → Integrations → Calendly Integration
  2. Toggle event types on or off as needed
  3. Click Save Changes
  4. Changes take effect immediately for new bookings

Refreshing Your Token

If you need to regenerate your Personal Access Token:

  1. Generate a new token in Calendly (following Step 1 above)
  2. Return to Gail’s Calendly integration settings
  3. Replace the old token with the new one
  4. Click Save

When you generate a new Personal Access Token, the previous token is immediately revoked. Update your Gail integration promptly to avoid service disruption.

Disconnecting Calendly

If you need to disconnect the integration:

  1. Go to Settings → Integrations → Calendly Integration
  2. Click Disconnect or Remove Integration
  3. Confirm the disconnection

Disconnecting Calendly will prevent your AI assistant from scheduling new appointments. Existing booked appointments in Calendly will not be affected.

Troubleshooting

Cannot Access Calendly Event Types

Symptoms: The integration connects, but no event types appear or bookings fail.

Solutions:

  • ✅ Verify your Calendly plan is Standard or higher (not Free or Essentials)
  • ✅ Confirm your Personal Access Token is correctly entered in Gail
  • ✅ Check that you have at least one active event type configured in Calendly
  • ✅ Try disconnecting and reconnecting the integration
  • ✅ Generate a new Personal Access Token and update Gail settings

Callers See Incorrect Availability

Symptoms: Available times don’t match your actual Calendly availability.

Solutions:

  • ✅ Review your Calendly availability settings and working hours
  • ✅ Check for date-specific overrides or blocked times in Calendly
  • ✅ Verify your timezone is set correctly in both Calendly and Gail
  • ✅ Ensure buffer times and minimum notice periods are configured as expected
  • ✅ Confirm that existing appointments are blocking time correctly

Some Event Types Not Showing

Symptoms: Expected event types are missing from the booking options.

Solutions:

  • ✅ Check that the event types are enabled in Gail’s Calendly integration settings
  • ✅ Verify the event types are active (not archived or hidden) in Calendly
  • ✅ Ensure the event types are set to “Public” or “Someone with the link” in Calendly
  • ✅ Refresh the integration by saving your settings again

Timezone Issues

Symptoms: Appointments are booked at incorrect times or in wrong timezones.

Solutions:

  • ✅ Verify your timezone is set correctly in Calendly account settings
  • ✅ Check that your Gail agent’s default timezone is configured properly
  • ✅ Test with different area codes to ensure timezone detection works
  • ✅ Review the call transcript to see what timezone was communicated to the caller

Authentication Errors

Symptoms: “Authentication failed” or “Invalid token” errors.

Solutions:

  • ✅ Verify your Personal Access Token hasn’t been revoked or expired
  • ✅ Check for any extra spaces when copying/pasting the token
  • ✅ Generate a new token and update Gail immediately
  • ✅ Confirm you’re using a token from the correct Calendly account

Best Practices

Event Type Organization

  • Create specific event types for different meeting purposes (consultations, demos, follow-ups)
  • Use clear, descriptive names that your AI assistant can communicate to callers
  • Set appropriate durations that include buffer time for preparation
  • Configure confirmation emails and reminders in Calendly for better attendance

Availability Management

  • Keep your Calendly availability settings updated to reflect your actual schedule
  • Use date overrides for holidays, vacations, and special events
  • Set realistic minimum notice periods to give yourself preparation time
  • Configure maximum events per day to prevent overloading your schedule

Integration Maintenance

  • Periodically review which event types are enabled for AI booking
  • Monitor scheduled appointments to ensure quality and accuracy
  • Update your Personal Access Token before it expires (if applicable)
  • Test the integration after making significant changes to your Calendly configuration

Customer Experience

  • Train your AI assistant to clearly communicate meeting types and durations
  • Ensure confirmation details are repeated before finalizing bookings
  • Set up Calendly confirmation emails with clear joining instructions
  • Include timezone information in all meeting communications

Need Help?

If you encounter issues or have questions about the Calendly integration:

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