Rewriting the Rules: Orlie Benjamin on Building Lasoh for a Better Guest Experience

In our June 2025 first-of-the-month bonus episode, we sat down with Orlie Benjamin, founder and CEO of Lasoh, to talk about guest relationships, revenue strategy, and the shift vacation rental operators must make to stay competitive in today’s market.

We first met Orlie at the VRNation conference, where her platform was already gaining attention for addressing a major gap in the industry: the need for smarter, guest-focused marketing technology built specifically for short-term rentals. 

In this conversation, Orlie shares why she left a successful corporate career to launch Lasoh and how her background with brands like American Airlines, Victoria’s Secret, and NetJets gave her a unique perspective on what operators truly need.

The 80/20 Rule in Hospitality

One of the most powerful insights Orlie shares is this: 80% of revenue often comes from just 20% of guests. This principle, widely used in retail and hospitality, highlights the importance of retaining and re-engaging past guests instead of relying solely on new bookings. Orlie explains that large hotel and airline brands have long understood this, and vacation rental operators, regardless of size, can benefit from applying the same playbook.

Lasoh: Designed to Strengthen Guest Relationships

At its core, Lasoh is a digital guest portal that integrates with property management systems (PMS) to give operators a more cohesive and branded way to communicate with guests. Unlike basic guidebooks, Lasoh offers a full interface that provides:

• Personalized trip details
  
  
• Local recommendations
  
  
• Upsell opportunities
  
  
• Group communication tools
  
  
• And most importantly, guest data capture at the time of booking
  
  

This early engagement allows operators to build trust before guests even arrive, setting the stage for a smoother stay and future relationship.

Navigating Platform Restrictions

With platforms like Airbnb tightening communication policies, many operators feel limited in how they interact with guests. Orlie addresses this head-on, explaining how Lasoh works around these restrictions without violating platform terms. By collecting opt-in guest information through PMS integrations and offering value outside of platform-specific messaging, operators can still build direct connections and protect their brand.

Retention Over Acquisition

Lasoh is not designed for guest acquisition. Instead, it focuses on retention marketing, a strategy that often yields better ROI and creates a more stable, long-term business. From automated review prompts to segmented email campaigns, Lasoh helps operators turn one-time guests into repeat visitors and brand advocates.

What's Next for Lasoh

Lasoh is gaining traction among early adopters who are ready to take ownership of their guest journey. Orlie is currently focused on:

• Expanding PMS integrations
  
  
• Creating partnerships with other STR tech providers
  
  
• Publishing educational content to help operators level up their marketing
  
  
• Introducing AI features carefully, with a focus on responsible and useful automation
  

Final Thoughts

This episode is a must-listen for any operator who wants to move beyond basic booking management and into the world of brand building, guest loyalty, and long-term profitability. Orlie’s story is a reminder that strong hospitality businesses are built on relationships—and with the right tools, even the smallest operator can compete at a higher level.

Watch the episode here: