How do you grow a short term rental or Airbnb management business without losing the human touch that makes guests book in the first place? In this episode of the STR Secrets Podcast, Breezeway founder and CEO Jeremy Gall breaks down the real role of AI and automation in vacation rental operations, and why automating everything could quietly kill your business.
Jeremy has spent 20 years building software for vacation rental operators. He founded FlipKey and grew it into one of the world’s largest vacation rental platforms before TripAdvisor acquired it in 2013. Today he runs Breezeway, the AI powered property operations platform behind more than 350,000 short term rentals worldwide. So when the person who builds AI tools for a living tells you not to automate everything, it’s worth hearing why.
He sits down with Mike Sjogren and Mike Reilly to explain the difference between service and hospitality, how to use AI to remove administrative work without “sterilizing” your guest experience, and why the human to human connection is now the biggest competitive edge a short term rental operator has.
What you’ll learn in this episode:
Why service is black and white but hospitality is in color, and how to deliver the kind guests remember
The “sterilizing” trap operators fall into when they over automate their Airbnb business
How to use AI and automation to eliminate repetitive operations work (cleaning, inspections, maintenance, scheduling) so your team can focus on five star guest experiences
Build vs buy: should you build your own STR software with Claude and AI, or use an existing platform? (plus the real cost of building enterprise grade tools)
The simple owner question that builds trust and improves owner retention
Why small operators can out hospitality the big national brands and win
How Breezeway uses embedded AI agents to automate the workflows behind five star stays
This conversation is for short term rental hosts, Airbnb property managers, vacation rental operators, and co-hosts who want to scale their portfolio while using AI the right way, to protect their edge, not erase it.
Jeremy Gall’s Bio
Jeremy Gall is a serial entrepreneur who has built software for vacation rental operators for twenty years. In 2006, Jeremy founded FlipKey, where he was responsible for all professionally managed inventory, and grew the platform into one of the world’s largest vacation rental businesses before TripAdvisor’s acquisition in 2013.
Jeremy is currently the Founder and CEO of Breezeway, the AI-powered property operations platform for short-term rental and hospitality operators. Breezeway automates the workflows that create 5-star stays, ensuring cleaning, maintenance, property care and service is done right. With embedded AI agents that handle the administrative burden, streamline communication, and control field operations, Breezeway helps teams execute to higher standards and deliver better guest experiences.
Connect with Jeremy Gall at:
https://www.breezeway.io/
https://www.instagram.com/breezeway.io/
https://www.linkedin.com/in/jeremiahgall