How Top STR Operators Scale with AI
Real tactics from operators running AI-powered portfolios and the founders behind the tools they use.
The fastest-growing STR operators aren't the ones with the biggest portfolios. They're the ones who've built AI into daily operations to spur growth and allow their team to keep up with it as they scale.
But knowing which tools are worth your time, getting them to actually talk to each other, and rolling it all out across a real team is still harder than it should be.
This webinar brings together operators who've rolled out AI across their own portfolios and builders who've helped thousands of STR operators do the same: Andrew Kitchell, Founder and CEO of Wheelhouse; Nate Klatt, Founder and CEO of HomeHop; and Jack Reipke, Head of GTM at Conduit. Moderated by Darren Carter, Head of Strategic Partnerships at Topkey.
Expect a candid, no-slides conversation on what AI actually looks like day-to-day, where operators are getting it wrong, and how to build a stack that scales.
If your serious about AI, this is the session to attend.
About the speakers
I've spent the last decade living inside the CRE, hospitality and short-term rental industry. Not just selling into it, but operating in it. I came up through sales at some of the companies that helped define the STR tech stack: Beyond Pricing, Wheelhouse, and Guesty. That foundation gave me a deep understanding of how operators think, what they're measured on, and where the real friction lives. Pricing strategy, portfolio growth, operational complexity, and the constant pressure to do more with less.
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I'm motivated by working with amazing groups of people on projects I love. Yes, I feel very fortunate that many/most days feel that way. Additionally, I love helping early-stage entrepreneurs get over the fundraising-gap and telling compelling narratives to investors in a manner that helps re-frame an opportunity. I live in keynote & dropbox paper, and love storytelling, ideally with a fun group of collaborators. Goal is to keep building a network & skills to take on bigger and bigger challenges.
I’m the CEO and co-founder of HomeHop Property Management, where we’ve scaled from 20 to 80 listings in 2024. I've also launched HomeHop Cleveland, a $2M fund investing in single-family short-term rentals in Northeast Ohio. We've grown our portfolio by prioritizing quality, technology, and design to stand out in a competitive market.
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Darren Carter is the Head of Strategic Partnerships at Topkey, the leading platform for helping property managers automate their finances. Before joining Topkey, he spent over 13 years at various technology companies, specializing in fintech and startups, including founding and selling his own company in 2020. He lives in Boulder, CO, with his wife, puppy, and baby daughter.
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