251. Meaghan Moylan

Behind The Scenes Of A Large-Scale Property Management Company

Today we’re giving you an insider’s view of a rockstar manager who is running a ton of rentals and has so much valuable experience and data to share. Whether you’re managing your own property, looking to partner with a management company or simply want to learn more about how it all works behind the scenes, today’s guest, Meaghan Moylan, is the perfect person to learn from when it comes to customer satisfaction and operational excellence.

An industry leader with 8+ years of experience in the STR space, Meaghan leads a team of passionate and entrepreneurial-minded professionals at The Outpost Group, a private investment office based in Jackson Hole, Wyoming. The company’s portfolio includes Outpost, Snake River Roasting Company, Terrain Landscaping and Snow Removal, O2 Cleaning, and Provisions Catering. Prior to her role with The Outpost Group, Meaghan held several leadership roles at 360 Blue, one of the largest luxury vacation rental businesses in the US. During her tenure with the company, Meaghan also assisted in the development of Key Data, a short-term rental data and benchmarking platform.

In this episode we talk about what it was like to be a reservationist at a large vacation rental company and how the property management business has evolved. She shares advice for working through rate change mistakes and fixing those inevitable errors. She explains the benefits of having laborers work for you in house versus contracting out, why it’s so important to be able to unlearn and adapt to evolving industries, how to set and evaluate KPIs for different sides of your business, what situations warrant a refund, and how to provide an exceptional customer experience. She also provides insight into what she’s learned post-COVID, what the current landscape is for vacation rental management, how to communicate effectively and honestly with the property owners, and what to think through if you’re thinking about bringing on a property manager.

Download a transcript of this episode.




It’s time for #strsharesunday! Today we are sharing Sunset Inn 😍

Second week in a row of sharing some amazing Vermont hosts! Maybe it’s time for a VT getaway 👀

Sophia and Ashley are the hosts of this beautiful circa 1787 inn. We LOVE their story! From high school besties to college besties at Boston University to roommates in NYC… to hosting biz besties! We love to see it!

Their experience in fashion and design really shines through in this historic inn. The photos are just so lovely! We just can’t stop staring at their gorgeous exposed wooden beams. The attention to detail and the mix of old and new have been woven with the utmost care.

Please give them some love. Check out their rooms and all the stunning renovations they’ve done (that kitchen though 😍)

Book with them during your next stay in Vermont!

We would love to feature YOU, so don’t forget to use #STRShareSunday to get your chance!

Together, Annette & Sarah are the dynamic duo behind the wildly popular podcast Thanks For Visiting, co-creators of the Hosting Business Mastery Method, & seasoned short-term-rental hosts.

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