Alex and Wes are a husband-and-wife team who not only call Big Sky home, but also invest deeply in its people, places, and future. Together, they built Two Pines over a decade ago on the belief that property management should feel personal, thoughtful, and positively impact the Big Sky community.

Alex is welcoming, kind, and calm under pressure—qualities she brings to her relationships with homeowners and guests, as well as to her current law school studies. Wes has a gift for making everyone feel at ease and at home, whether he’s working with clients, greeting guests, or sharing his love of the mountains. Alex and Wes both share a love for Montana and feel grateful to be raising their daughter, Hope, in this beautiful place. 

Rooted in Community

Their love for Big Sky goes far beyond business. Alex serves on the board of Haven, the local domestic violence shelter, while Wes is a board member at Morningstar, Big Sky’s beloved community daycare. Two Pines is also a major sponsor of the Big Sky Biggie, the town’s signature mountain bike race, as well as other events, including film festivals, Moonlight Community Foundation events, and various local non-profit events throughout the year. Supporting local organizations and events is at the heart of their work, because to Alex and Wes, caring for homes means also caring for the community that makes Big Sky such a special place to live and visit.

A Team That Cares for Every Detail & Knows Big Sky

What makes Two Pines unique is that our employees don’t just work in Big Sky, they live here too. We invest heavily in employee housing so that our team can remain an integral part of this community. That means when homeowners or guests need support, they’re not dealing with a distant call center or a company led from across the country; they’re talking to neighbors who are right here, ready to help.

Under Alex and Wes’s leadership, Two Pines has built a team that blends professionalism with true Montana hospitality. Our operations crew is the boots-on-the-ground heartbeat of the company: from our skilled in-house maintenance team, who can fix anything, to our detail-oriented inspectors who carefully check each home before and after every stay. Our property managers know our clients’ homes inside and out, while our guest services team combines local knowledge with lightning-fast response times to ensure every guest feels cared for from their first inquiry to their final farewell.

Behind the scenes, our administrative team ensures everything runs smoothly. Our owner client experience specialists make onboarding simple and stress-free, and then provide personalized care and clear communication throughout your partnership with us. Working closely with property managers, they ensure that every home, every stay, and every owner experience meets the high standards that Two Pines is known for.

For Alex and Wes, Two Pines is more than property management, it’s a way to honor Big Sky by protecting its homes, welcoming its visitors, and strengthening the community they love.