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Seasonal/Holiday Lead Follow-up Automation

The Seasonal/Holiday automation handles inquiries for peak travel periods with heightened urgency and provides alternative options when availability is limited.

Overview​

Purpose: Convert high-value peak season inquiries while managing availability constraints.

Trigger: Inquiry for peak season dates, holidays, or special events.

Channels: Phone call (immediate), followed by email with alternatives.

Setup Instructions​

  1. Navigate to Automations in your SendSquared dashboard
  2. Click + Create New Automation
  3. Select Peak Season Inquiry from the template library
  4. Configure the automation with the following nodes:

Step 1: Configure Peak Period Detection​

  1. Select the Date-Based trigger
  2. Define peak seasons:
    • Summer (June-August)
    • Winter holidays (Dec 20-Jan 5)
    • Spring break (regional)
    • Major holidays (Memorial Day, July 4th, Labor Day)
    • Local events and festivals

Step 2: Assign Priority Urgency​

  1. Add Priority Level based on:
    • Dates within 30 days: URGENT
    • Major holidays: HIGH
    • School holidays: MEDIUM
    • Festival dates: EVENT-SPECIFIC

Step 3: Create Urgency Response​

  1. Add immediate Task Creation for sales team
  2. Configure phone call within 1 hour
  3. Prepare alternative date scripts

Phone Call Script Template​

[URGENT: Peak Season Inquiry - CALL IMMEDIATELY]

Lead Priority: HIGH
Response SLA: 1 hour

Guest Information:
- Name: [Name]
- Dates Requested: [Dates]
- Property Interest: [Property]
- Group Size: [Count]
- Contact: [Phone]

Opening Script:
"Hi [Name], this is [Agent] from [Company]. I'm calling about your inquiry for [Date Range]. I wanted to personally assist since these are our busiest dates."

If Unavailable for Requested Dates:
1. "While [Property] is booked for those exact dates, I do have excellent alternatives..."
2. Offer date flexibility:
   - "We have availability the week before/after"
   - "A longer stay actually saves you money"
   - "Tuesday-Sunday often works better than Mon-Fri"

3. Suggest similar properties:
   - Same location, similar amenities
   - Comparable size and features
   - Special holiday packages

Email Template (Follow-up)​

Subject: URGENT: Limited availability for [Holiday/Season]

Dear [Guest Name],

Thank you for your inquiry about staying with us during [Holiday/Season]!

Your requested dates: [Dates]
Status: [Limited/No availability - immediate action needed]

Due to high demand for these dates, I want to ensure you secure accommodation:

IMMEDIATE AVAILABILITY:
Option 1: [Property Name]
• Similar amenities to your inquiry
• [Dates available]
• Rate: $[Amount] (Special holiday rate)
• [Unique features]

Option 2: [Property Name]  
• [Dates slightly different]
• Rate: $[Amount] (Lower than peak)
• [Value proposition]

WAITLIST OPTION:
• [Original Property] - We can place you first on the waitlist
• Cancellations possible up to [Date]
• We'll check daily and contact you immediately

ALTERNATIVE DATES:
If you're flexible, consider:
• Week before: [Dates] - Save 20%
• Week after: [Dates] - Save 15%  
• Extended stay: [Longer dates] - Save 25%

BOOK NOW to secure your spot:
[Direct Booking Link]

These properties typically book within hours during peak season.

Call me directly: [Phone] for immediate assistance

Best regards,
[Vacation Specialist]
[Management Company]

Peak Season Strategies​

For Sold-Out Properties​

  1. Waitlist Management:

    "I can place you first on our cancellation list. We typically see 2-3 cancellations per property within 30 days. No commitment required."

  2. Package Approach:

    "While [Property A] is booked, I can combine two smaller units next to each other. This actually gives you more space for less money."

  3. Extended Stay Incentives:

    "If you can stay 7+ days, we have a luxury property that requires minimum stay. You'd save $[Amount] over your requested shorter stay."

Holiday-Specific Messaging​

New Year's Eve​

Subject: Ring in 2025 with us - Limited NYE Availability

Last 3 properties available for NYE:
• Ocean view with private deck
• Downtown loft with rooftop access
• Beach house with outdoor area

All include NYE celebration package. Book by midnight to secure.

Summer Memorial Day Weekend​

Subject: Memorial Day Weekend - Book Now or Miss Out

Pool access fills first. Only 2 properties left with:
• Private pool/pool access
• Sleeps [X]
• Available May 24-27

Act fast - summer bookings typically secured by March.

Seasonal Communication Cadence​

90+ Days Before Peak:​

  • "Early bird secured" confirmation
  • Property upgrade opportunities
  • Add-on service booking

60-89 Days Before:​

  • "Secure your remaining dates"
  • Upgrade reminders
  • Local event tickets availability

30-59 Days Before:​

  • Final availability check
  • Upsell opportunities
  • Pre-arrival concierge services

Under 30 Days:​

  • Extreme urgency messaging
  • Last-minute cancellation hunting
  • Premium pricing for remaining inventory

Best Practices​

  • Prioritize peak season leads above all others
  • Have alternative suggestions ready immediately
  • Create FOMO (Fear of Missing Out) naturally
  • Offer flexible solutions beyond original ask
  • Follow up within 1 hour max
  • Use multiple channels for urgency
  • Track cancellations constantly

Common Peak Season Issues​

  1. Double Bookings:

    • Clear calendar immediately
    • Offer compensation when errors occur

  2. Rate Shopping:

    • "Peak rates are market-driven and consistent"
    • Emphasize included value during holidays

  3. Minimum Stay Requirements:

    • Explain local regulations/policies
    • Show value of longer stays