As AI tools and automated platforms flood the short-term rental industry, the greatest risk to your business isn't lack of software, it's the rapid erosion of trust. In this episode of The Accommodation Show, Bart Sobies sits down with Margot Schmorak, CEO and co-founder of Hostfully, to examine what it takes to build a truly resilient accommodation business heading into 2027.

Margot opens up about Hostfully's internal tech evolution, candidly discussing why they refocused on product after underinvesting in engineering for several years, why they strictly hire senior engineers in an AI-driven environment, and why they are completely comfortable letting 1,000-unit enterprise clients walk away to focus obsessively on growing 5-to-30-unit managers.

Drawing from her recent stays across Colombia and Greece, Margot also breaks down why operators must stop orienting strictly around physical inventory and start designing their operations around traveler personas. Plus, we explore the reality of AI adoption: why true automation is still unfinished, why operators must "squint" at data, and how to maintain authentic human accountability.

Guest: Margot Schmorak, CEO & Co-founder of Hostfully
Website: https://www.hostfully.com

In this episode, we discuss:
00:00 - Conference Season Wrap-Up & Global STR Stays
02:30 - Hostfully's Engineering Overhaul & Strategic Investment
05:15 - Why Hostfully Refuses to Hire Junior Engineers in the AI Era
08:40 - The "All-in-One" Myth: Why Hostfully Doesn't Target 1,000-Unit Enterprise Portfolios
12:10 - Apple vs. Google: Curating In-House Tech vs. Wild West Marketplaces
16:00 - Travel Insights: Cartagena, Athens, and Bogota
19:30 - Orienting Around Clientele vs. Physical Inventory
23:15 - The Two Waves of Tech: Unfinished Automation vs. Sentiment Listening
27:00 - Why AI Is Never "Set and Forget": Training Intercom's Fin
30:45 - Looking Ahead to 2027: The Erosion of Trust in Data & Software
34:20 - The Importance of "Squinting" at AI Outputs and Self-Assessment

Show links
Hostfully: https://www.hostfully.com
The Accommodation Show: https://www.theaccommodationshow.com
Join the mailing list: https://news.theaccommodationshow.com/
Accommodation Owners and Managers Facebook Community: https://bit.ly/AMoFacebookCommunity
Connect with Bart Sobies: https://www.ibooked.online/bart/
Come to STRIVE: https://www.striveconferences.com

Hotel, BNB and STR owners: need more direct bookings or a brand new website? https://www.ibooked.online

Disclaimer: The content shared on this podcast reflects personal opinions and insights. It is not intended as legal, financial, or investment advice. Always consult with licensed professionals before making decisions.