Updated on September 5, 2024

Meaghan Moylan, The Outpost Group, RR Summit

For The Outpost Group in Jackson Hole, Wyoming, creating an incredible guest experience and supporting local businesses are one and the same. What was originally just one business, Outpost Vacation Rentals, has expanded into a holding company of six businesses. These include a gear and household goods delivery service, a landscaping and snow removal company, even a local coffee roaster – and then some. 

In a session at the winter 2023 RR Summit, Outpost Group Executive Director Meaghan Moylan illustrated how their deep commitment to local businesses and jobs in Jackson Hole created a unique and satisfying destination experience that keeps guests coming back. Here are three takeaways on how you can replicate their best practices in your destination.

To watch the entire session, join or log into the RR Network BETA and head to the Replays & Downloads library.

1. Curate local experiences

Build connections with local businesses and encourage your guests to visit local businesses that help make your destination unique. This could be as easy as including a $5 gift card to a local coffee shop or restaurant when guests check in, Meaghan said. This simple gesture helps increase foot traffic at local businesses and also gives your guests a local culinary or coffee experience – the tiny details that make a stay memorable. By ingratiating yourself to local businesses, you also build goodwill toward vacation rentals in your community.

“Supporting our mountain region and the integrity of our town is so important to us, and so we started to think through how we can educate our guests on taking care of our community while they’re here, which hopefully benefits our reputation in the long run and makes guests feel a little bit more welcome,” Meaghan said.

Beyond directing guests to local businesses, Outpost Group engages in the community to glean ideas for how to curate local experiences for guests and how to improve the impact guests have on local natural resources and residents. For example, the holding company contributes to and gets involved with local nonprofit organizations and listens to what people have to say about vacation rentals. This feedback provides insights on how guests are impacting the local community and ways to improve the interactions between guests and local residents.

RR Summit Replays in the RR Network

For more examples of how Outpost Group has enhanced the guest experience, improved the local community, and protected local natural resources, watch the full replay of this session inside the RR Network.

2. Empower your team to take a community-centric approach

Creating an enticing local experience also means empowering your team and guiding them to mindfully look at everything they do through the lens of guest experience, Meaghan said.

Communicate transparently with your team while you’re implementing a new process. Explain why a partnership might be worth it in the end. “It’s really helpful for them to understand that big picture,” she said.

In addition, listen to feedback from your team. “They’re members of your community as well,” Meaghan said.

“Make sure employees feel heard and know what direction your boat is rowing in. If you come in every single day and you’re expecting them to row and you’re not telling them where you’re going as a business, it’s really difficult to get everyone rowing in the same direction.” 

For more strategies for guest and employee retention, explore the libraries in the RR Network.

3. Measure your impact and adjust  

Measure your impact by looking at guest, employee, and community feedback. When you see consistent data or feedback that something isn’t working, don’t be afraid to pivot, Meaghan said.

Read guest reviews and respond to the reviews on every single platform where your vacation rentals are listed, and send out a survey to your guests to understand what they’re looking for and then cater to their needs.

“It’s OK if you partner with a company for a gift card exchange, and your guests have a bad experience and you decide to cancel that partnership and go in a different direction,” Meaghan said “We need to understand what our guests’ needs are because we are different from our guests.”

In addition, set measurable goals. Limit yourself to three or four attainable goals, like increasing your direct bookings by 10% or increasing repeat guests from 30% to 50%.

“Move deliberately and intentionally, but make sure that you aren’t in over your skis, that your team is in the right place, that you have processes in place before you expand, that you feel really comfortable with your existing offerings, that this isn’t going to jeopardize the experience that you can offer your owners and your guests and your employees,” she said. “Balance expansion with sustainability.”

Check out “Best practices for managing your short-term rental from afar” by joining or logging into the RR Network Beta and heading to Articles & Guides 

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