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Direct Booking Winback

Your past guests are your cheapest bookings, and their data sits scattered across your PMS, OTA aliases, and WiFi captures, rarely segmented or emailed in time. Direct Booking Winback turns that history into tight, consent-clean campaigns: it segments the guests worth reaching, matches them to soft inventory, drafts copy that sounds like you and not a coupon machine, and shows the OTA fees you would save.

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How to use this template

  1. Hire the template in your Sidekicks dashboard
  2. Connect your PMS, your direct-booking site, and your email or SMS channel
  3. Confirm your consent sources so only reachable guests are eligible
  4. Go live in draft, nothing sends without your approval

What this does

  • Builds the eligible list from consented contacts only, and never blasts the whole database
  • Segments by stay type, market, season, sentiment, and repeat potential
  • Excludes the bad stays, the unresolved complaints, the unpaid balances, and the unsubscribed
  • Matches each segment to real available inventory and a soft demand window
  • Shows the expected revenue and the OTA fees saved, separately, and drafts copy in your voice

Saves

  • The repeat bookings you leave on the table because the guest data never got segmented
  • The 15% or more in OTA fees on every stay you move to direct

Workflow

Trigger
Monthly, and when a soft window appears
Scans for campaigns each month by market and season, and kicks in when an upcoming period is pacing soft with open inventory.
Tool call
Pull guests and availability
pms.list_guests() + reservations + get_availability() + consent status · the history, the sentiment, and the nights that need filling.
Prompt
Segment and match
Builds tight segments from consented guests, filters out the bad stays and the complaints, and matches each to real inventory and the campaign goal.
Draft
Draft the campaign
Email or SMS copy that sounds like a property manager, an offer with clear rules, and the expected revenue next to the OTA fees saved.
Approval
You approve the send
You sign off on the segment, the offer, and the copy. Only a pre-approved evergreen sequence with consent filters locked runs on its own.

More Sidekicks to explore.

Money Leak FinderA weekly list of charges you probably missed or mis-billed.Rate CheckShows how your rates compare to similar rentals nearby.Missed Revenue FinderFlags high-demand dates where your price is below the market.Underpricing CheckFinds listings priced like a weaker neighborhood than they sit in.

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Every template drafts first. You approve what matters.

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