Winner of The Shortyz 2026 Best Travel Influencers of the Year

Orlie Benjamin

Orlie Benjamin Profile Photo

Founder & CEO

Orlie Benjamin knows what it's like to lay awake at night worried about a potential 1-star review. As both a hands-on property manager and former Fortune 500 marketing executive, she built Lasoh because she was tired of cobbling together spreadsheets and generic tools to manage marketing strategies.

Before founding Lasoh, Orlie found herself in the trenches of property management, dealing with everything from last-minute cancellations to guests who couldn't figure out the smart lock. But her background at American Airlines, Victoria's Secret, and NetJets showed her what sophisticated guest relationship management and marketing could look like. She realized vacation rental operators were stuck with tools designed for hotels or generic CRMs that didn't understand their unique challenges.

Now she's on a mission to give every property manager, whether they have 2 units or 2000, access to the same marketing technology that billion-dollar hospitality companies use to build guest loyalty and maximize revenue.

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July 31, 2026

1st of the Month Wrangle: How Direct-to-Consumer Thinking Can Shape Vacation Rental Marketing with Orlie Benjamin and Patti Ziegler

In this third episode of First of the Month Wrangle, presented by Lasoh, we are joined by Orlie Benjamin, Founder and CEO of Lasoh, and Patti Ziegler, Orlie’s longtime mentor and former leader at Scotts Miracle-Gro. Before building Lasoh, Orlie worked with Patti across direct-to-consumer marketing, brand building, innovation, and partnerships. That experience shaped how she thinks about customer relationships, distribution, and the value of knowing the people behind each purchase. That sam...
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May 31, 2026

1st of the Month Wrangle: Can We Stop Marketing Properties and Start Marketing to People? with Lasoh CEO Orlie Benjamin

Send us a message! In this second episode of First of the Month Wrangle, presented by Lasoh, Alex & Annie are joined again by Orlie Benjamin, Founder and CEO of Lasoh, to continue the conversation around vacation rental marketing and what it takes to make it more effective, more personal, and more guest-centered. This time, the conversation focuses on a simple but important question: can we stop marketing properties and start marketing to people? For many vacation rental operators, marketing ...
Guests: Orlie Benjamin , Lasoh
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April 1, 2026

1st of the Month Wrangle: What's Missing from Vacation Rental Marketing, with Lasoh CEO Orlie Benjamin

Send us a message! We’re kicking off a new special series, First of the Month Wrangle, in partnership with Lasoh, where we’ll dig into the strategies, systems, and blind spots shaping one of the most important and often misunderstood areas of vacation rentals: marketing. Throughout the series, Alex & Annie will be joined by Orlie Benjamin, Founder and CEO of Lasoh, a vacation rental marketing platform built to help operators drive more direct bookings and increase profit through deeper relati...
Guests: Orlie Benjamin , Lasoh
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June 1, 2025

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

Send us a message! In our first-of-the-month bonus episode, we are joined by Orlie Benjamin, founder and CEO of Lasoh, a marketing technology platform designed to help vacation rental operators own their guest relationships and drive direct revenue. Lasoh provides a branded digital guest portal and integrated CRM that allows operators to engage with guests from the moment of booking, offer upsells, and run smart, automated campaigns. Orlie shares how her background in corporate marketing and ...
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May 5, 2025

Live from VRNation: Unpacking The Real Story

Send us a message! Alex & Annie bring you behind the scenes at VRNation 2025 to explore direct booking strategies, industry growth, tech innovation, and the evolving role of associations in vacation rentals. Recorded live in Austin, Texas, this special bonus episode captures real-time insights from the conference floor. Alex & Annie had on-the-spot conversations with some of the industry’s most influential voices and rising innovators to unpack the real story behind what’s shaping the vacatio...