Let’s be honest—talking about how to drive direct bookings has probably been on the agenda since hospitality conferences were held in fax machine-friendly ballrooms. And yet, here we are in 2025, still debating, still refining, and (hopefully) getting smarter about it.

That’s exactly what we set out to do during our roundtable at the HSMAI Commercial Strategy Conference in Singapore. The topic? How to compete more strategically in a world where you’re up against not only nearby hotels, but also dominant OTAs and well-connected travel agents.

We kept things open, interactive, and full of practical advice—because while the theme of direct bookings isn’t new, the tools and tactics absolutely are. Three core strategies took the spotlight: Loyalty, Personalization, and Segmentation.

Let’s dive in…

Loyalty: Make It Local, Make It Matter

Generic point systems? Yawn. Guests today want loyalty benefits that feel meaningful—and memorable. We explored ideas like:

Local experiences: a wine tasting, a wellness class, or early access to a rooftop yoga session.

Property-specific perks: not just another discount, but something that feels truly special—like my recent favourite: Luxury Hours—a two-hour window at the hotel’s private bar with complimentary drinks and bites. Simple, memorable, and totally on-brand.

Takeaway: Loyalty is no longer about the punch card—it’s about personal touch, place-based value and instant rewards

Personalization: From Creepy to Clever

Done right, personalization builds trust and relevance. Done wrong, it feels invasive. We focused on the former, with ideas like:

• Tailored offers based on travel dates and intent (hello, Valentine’s Day package!).
• Curated extras that highlight local gems—think Michelin-starred dinners or nearby cultural experiences.

Takeaway: The best kind of personalization feels like a thoughtful suggestion, not a sales pitch.

Segmentation: Precision Over Blanket Discounts

• “Everyone gets 10% off” won’t cut it anymore. We talked about using smart segmentation to create offers that land:
• Families vs. solo travelers vs. business guests: each has unique needs and timing.
• Low-demand periods? Use creative packaging to drive bookings without eroding rate.

Takeaway: Matching the right message to the right guest at the right time is still one of your most powerful tools.

Final Thoughts: Old Topic, Fresh Thinking

Yes, direct bookings have been the holy grail for years—but what’s changed is the way we get there. The magic lies in the execution: being strategic, guest-focused, and unapologetically unique in what you offer.

Our roundtable didn’t reinvent the wheel, but it reminded us all why the wheel works—and how a few well-placed spokes (loyalty, personalization, segmentation) can keep it rolling smoothly toward profitability and guest satisfaction.