Beyond the Slopes: How to Turn a Loyal Guest Into a Portfolio Loyalist
Ellis Connolly, CRO at Laasie
There’s nothing quite like a regular. The kind of guest who knows the front desk team by name, requests the same suite every visit, and books their seasonal trips like clockwork. They’re the heartbeat of your RevPAR.
But here’s the twist: while you’re patting yourself on the back for capturing their loyalty to one of your properties, they’re out skiing at three other mountains every winter… just never at yours.
This is the tale of The Devoted Regular...the guest who is emotionally loyal to your brand at one location, but hasn’t connected the dots to the rest of your portfolio. And let me tell you, if you’re not actively designing their next journey, someone else’s booking engine will.
Let’s fix that.
Meet the Devoted Regular (And Her Untapped Potential)
Let’s call her Caroline.
Caroline has stayed at your Summit Pines Lodge in Jackson Hole every Presidents’ Day weekend for four years. She always books a deluxe king with a fireplace, hits the spa before skiing, and loves the peppermint hot chocolate from the lobby bar. Her lifetime value? Over $14,655 a year.
But here’s what your CRM just surfaced: She follows two other ski destinations on Instagram. She tags a different resort in Colorado each March. And last year, she posted an après-ski story... from Stowe.
Caroline isn’t just your best customer... she’s also your biggest missed opportunity. And she doesn’t even know it.
Cross-Property Loyalty Is the Next Big Revenue Driver
We’ve entered the era of portfolio personalization. Your most valuable guests don’t just want a punch card—they want a curated journey across your collection.
Here’s the truth: most hotel groups aren’t maximizing cross-property value because their loyalty strategy is property-specific. Each hotel guards its CRM data like a local secret, and no one is proactively saying:
“Hey Caroline! You already love Summit Pines. Why not check out our sister lodge in Lake Tahoe this spring? Your room type and perks are waiting.”
That’s the magic we enable with Laasie guest-centric loyalty that travels with your guest, wherever your flag flies.
Identify Your Carolines
Your first move? Stop thinking like a spreadsheet and start thinking like a storyteller.
With Laasie, we use behavioral and transaction data to surface “Devoted Regulars” across your properties. Our system connects:
Repeat stay patterns
On-property reward behavior (spa visits, upgrades, F&B)
This paints a full picture of the guest, not just where they have stayed, but where they might go next.
When the CRM flagged that Caroline had visited your Jackson Hole, Santa Fe, and Aspen web pages all within 30 days we didn’t see curiosity. We saw intent. That’s when you strike.
Curate the “The Alpine Path Milestone”
Think of it like a Netflix recommendation engine, but for meaningful travel experiences.
Laasie enables you to build dynamic, cross-property campaigns based on past behavior. So if Caroline loves your Hunter property and books spa services like clockwork, here’s what she gets:
“Your next peak awaits. As one of our Hunter regulars, we’ve reserved your preferred room type and spa perks at our Lake Placid lodge, plus a member-exclusive reward to make your first stay even sweeter.”
This isn’t mass email marketing. It’s loyalty storytelling. You’re not selling her on a new property. You’re inviting her deeper into the brand she already trusts.
Make Her Feel Known... Everywhere
This is where most programs fall apart.
Even if you get the guest to book another property in your portfolio, the experience resets—no preferred room pre-assigned, no spa profile carried over, no welcome gift that says “We remember you.”
That’s the quickest way to kill brand affinity.
With Laasie, her preferences travel with her:
Her favorite room layout and floor
Her pillow preference (hypoallergenic, obviously)
Her membership status and past perks
Her rewards and redemption history
Everything’s unified across the portfolio. It’s not a new stay. It’s a new chapter.
And when she checks in, the front desk greets her like they’ve known her for years. Because thanks to the CRM, they basically have.
Reward Her for Expanding the Relationship
Here’s the part where you turn a good guest into a superfan.
Laasie lets you layer instant, personalized rewards that feel like gifts... not transactions.
First-time stay at a sister property? Offer a local dining experience or free lift pass.
Booked 3+ properties in a calendar year? Surprise her with a curated “Explorer” reward tier.
Refer a fellow skier? Drop both of them a $50 gear credit.
The more they explore, the more they earn, not in points, but in relevant, frictionless perks that feel like an extension of the experience.
This kind of loyalty isn’t about climbing a ladder. It’s about moving horizontally across your brand and being delighted at every stop.
Five Plays to Launch a Portfolio Loyalty Strategy This Quarter
Identify your top 10 single-property regulars Pull CRM data and find your “Carolines.” Prioritize by LTV and repeat behavior.
Build a branded journey framework Name it something elegant: “The Alpine Path,” “The Seaside Circle,” “The Urban Explorer Club.”
Audit CRM integrations Ensure preferences, room types, and rewards are synced across properties. If they’re not, Laasie can help stitch it together.
Design onboarding campaigns Send triggered “Try a Sister Property” emails to regulars with stay history and tailored rewards.
Track movement and reward accordingly Celebrate guests who stay at 2, 3, 4 properties. Don’t tier them... just surprise and delight them.
Final Word from the CRO’s Desk
There’s something beautifully simple about a guest who comes back year after year. But there’s something even more powerful about a guest who brings that loyalty with them to every flag you fly.
If your loyalty program ends at the lobby, you’re leaving revenue on the runway. Caroline isn’t just a Hunter loyalist. She’s a Alpine Path devotee waiting to happen. All she needs is a reason and a reward to say yes.
And that’s where Laasie comes in.
Want help mapping your top cross-property guests and building a journey they’ll love? Let’s chat. I’m Ellis Connolly, CRO at Laasie and we’re here to help you make loyalty personal, portable, and profitable.