Winner of The Shortyz 2026 Best Travel Influencers of the Year

Jeremy Gall

Jeremy Gall Profile Photo

Founder & CEO

Jeremy Gall is a serial entrepreneur with a history of delivering great software products to vacation rental operators over the past fifteen years. In 2006, Jeremy founded FlipKey, where he was responsible for all professionally managed inventory, and grew FlipKey into one of the world’s largest vacation rental businesses before TripAdvisor's acquisition in 2013.

Jeremy is currently the Founder & CEO of Breezeway, the industry-leading platform where the hard work of hospitality gets done right and operators can deliver on their guest experiences. Started in 2016, Breezeway’s software and mobile apps help thousands of short-term rental managers and hospitality operators increase their operational efficiency, eliminate hours of manual work, and boost service revenue.

Jeremy has been featured on the Today Show, discussing vacation home rental safety and promoting quality standards for the vacation rental industry. An avid traveler and vacation rental advocate, he is a regular contributor to VRMA, VRM Intel, and other travel industry publications.

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Aug. 26, 2026

Why the Future of Vacation Rentals Starts with Better Operations with Jeremy Gall of Breezeway

In this episode, Alex & Annie sit down with Jeremy Gall, Founder and CEO of Breezeway, to explore how the continued professionalization of vacation rentals is raising the bar for operations. Jeremy shares what led him to tackle one of the industry's most complex challenges: coordinating the people, properties, and workflows behind great hospitality. The conversation explores how rising guest expectations, greater owner scrutiny, and advances in technology are changing what it takes to operate w...
Guest: Jeremy Gall