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Key Takeaways
Fix the guest experience before you scale outbound: List size is a vanity metric. Conrad worked with a manager whose open rates topped out under 10% — bad Google reviews, corners cut everywhere, one roll of toilet paper for a week-long stay. Those guests booked on price, and no volume of outbound brings them back. Meanwhile he opens every email from his own Kiawah stay hoping for an excuse to rebook.
One-to-one calls to a VIP list are a moneymaker: A North Carolina client tags everyone who has stayed three-plus times, and by spring anyone unbooked for summer gets an outbound call and a voicemail drop. That motion alone drives tens of thousands of dollars in weekly revenue — most of these guests simply got busy. Point the effort at hand-raisers like checkout abandons, and ask for the booking on the call.
Text first so your call actually gets answered: Almost nobody answers an unknown number. Text at 1 p.m. — Paul from the reservations team, calling around 3 with some special fall rates — and your pickup odds jump. And stop filtering tactics through your own habits: Conrad dismissed direct mail too, until testing proved it works on the people it’s built for.
A three-year-old SMS list can outbook a 20-year email list: Conrad’s Myrtle Beach client attributes more monthly bookings to an SMS list of about a thousand people than to an email list five to seven times larger and two decades old. The trade-off is intimacy: your message sits next to texts from mom, so the unsubscribe trigger is fast. Respect the frequency and SMS beats email by a wide margin.
Always have an offer — mattress stores are never not on sale: Generic book-my-place messages give nobody a reason to act. Mattress stores invent a new sale every week because hooks work, so build a rotating calendar of reasons to reach out. Luxury brands that refuse to discount can add value instead. In years of client work, Conrad can name maybe one company that overdid its offers — everyone else underdoes them.
- A dated sale (Labor Day, end of summer)
- Early check-in or late check-out
- A waived fee
- An added experience or welcome package
Judge email newsletters as top of funnel, not last click: Guests click through ten emails without booking and the channel still worked — you planted a seed, and that person moves down the funnel far faster than a stranger scrolling past an Instagram ad. Paul still sees February campaigns show up in July booking paths in Google Analytics. Consistency beats send-time tinkering: pick a rhythm and show up every month.
Not all email addresses are equal: Segment by source, not just by stay history. A past guest, a StayFi capture, and a giveaway entry carry completely different intent — giveaways grow the list fast, but the average address is worth much less. Layer stay-based segments — the one-bedroom condo guest versus the ten-bedroom group — on top when an offer calls for it.
Book your own property and audit the automated messages: Stay in your own rental and log every message from confirmation to checkout. Conrad has received a guidebook email and a PMS confirmation carrying two different door codes on the same stay. Overlapping sequences stack fast — enough enrollments and 12 workflows become 24 messages burying the operational ones — so build rules-based exceptions that suppress one flow when another fires.
You’re probably under-messaging, and Airbnb’s fee proves the math: Most managers never press the gas for fear of spamming — one manager Conrad talked to gets 40% open rates and emails every four months. Anchor the cost against the alternative: $25,000 of those bookings through Airbnb costs about $3,875 at the 15.5% fee, far more than a week of wages for the person dialing. And the list is the one asset no platform can take from you.
What We Cover In This Episode
Conrad and Paul make the case for outbound as the neglected leg of direct booking marketing — one-to-one calls and texts to past guests, broadcast SMS, newsletter-style email, and the automated sequences underneath it all — plus how to anchor the cost of doing it against Airbnb’s commission.
