Automated Trip Anniversary Outreach
Every morning, WebRun opens TravelJoy, finds past clients reaching the one-year anniversary of a completed trip, drafts each a warm, personal note in Gmail referencing where they went and inviting them to plan the next one, leaves every draft unsent for you to review, and pings you on Telegram with who is ready for rebooking outreach.
How do I do trip-anniversary rebooking outreach to past clients automatically?
Every morning, WebRun opens TravelJoy and finds past clients reaching the one-year anniversary of a completed trip. It drafts each a warm, personal note in Gmail referencing where they went and inviting them to plan the next one, leaves every draft unsent for you to review, and pings you on Telegram with who is ready for outreach.
- Past clients get a timely, personal nudge a year out, not silence
- Each note is drafted and waiting, so you just personalize and send
- Repeat bookings rise without manually combing through old trips
Built for travel agencies · travel advisors · host agencies · independent contractors
What does WebRun do on every run?
The exact actions WebRun takes, in order - in plain language, so you can adjust anything.
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WebRun signs in and gets to work
Opens
traveljoy.comin a real browser with your saved login - no setup, no API keys. -
1
TravelJoy - find trip anniversaries
traveljoy.com
WebRun opens TravelJoy to find past clients reaching a trip anniversary. - Open TravelJoy and open completed trips reaching their one-year return anniversary this week
- Read each trip for the destination, travel party, and the occasion if noted
- Capture the client, last destination, and anniversary date for each
Done when Every past client hitting a trip anniversary has been listed with their last destination.
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2
Gmail - draft rebooking outreach
gmail.com
WebRun drafts a personal anniversary note for each past client and leaves it unsent. - Draft each client a warm, personal note referencing their last trip and inviting them to plan the next
- Suggest a relevant next destination or season where it fits naturally
- Save every message as a draft and leave it unsent for you to review before it reaches a client
Done when A personal rebooking-outreach draft sits ready in Gmail for every client with an anniversary.
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3
Telegram - ping who is ready
telegram.org
WebRun pings you with past clients ready for anniversary outreach today. - Send you a short Telegram list of past clients ready for anniversary outreach today
- Note each client's last destination so you can add a personal touch before sending
- Note that the outreach notes are waiting as drafts in Gmail for review
Done when You have today's rebooking-outreach list on Telegram.
How is each run configured?
Secure by default
Connect once, stays signed in
WebRun signs in once and keeps each session in a persistent environment, so every run picks up right where it left off.
Every action is checked against this policy before it runs.
Questions, answered
Will it email past clients without me?
No. WebRun only drafts each anniversary note in Gmail and leaves it unsent. You read every message and click send, so no outreach reaches a past client without a person approving it first.
How does it pick who to contact?
It reads completed trips in TravelJoy each morning and surfaces clients reaching the one-year anniversary of their return, so outreach lands when they are most likely to be daydreaming about traveling again.
Can it make each note personal?
Yes. It references each client's last destination and travel party from TravelJoy and drafts in your voice, so every note feels personal rather than a generic blast, and you can tweak it before sending.
Related templates
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