In this episode of the Everything AI in Travel podcast, we dive deep into the vacation rental world and the fast-changing landscape of property management systems (PMS) with guest Shahar, founder of Boom, an AI-native operating system for vacation rental managers.
From Miami, Shahar shares how he went from doing hundreds of millions in real-estate deals to “accidentally” building a vacation rental management company—then vertically integrating management, construction, cleaning, and a $50M fund—before spinning out the tech and ultimately selling his management business to Casago. Today, that same tech powers Boom, now live in 20 countries across five continents.
We talk through:
- What PMS looked like in 2017 – basic channel managers and unified inboxes – and why that wasn’t enough for serious operators
- Why traditional PMS + a dozen disconnected tools (pricing, tasks, guest comms, accounting, etc.) breaks down—and how Boom’s “business as software” view ties it all into one data model
- How AI agents can only work if all the operational data is structured and connected (cleaning, tasks, GPS, inspections, payments, owner P&L, trust accounting, reviews and more)
- How Boom is already automating 80% of guest communication, and what true agentic AI looks like in property ops
- Why their ICP starts at 50+ properties, what they’re seeing from leading operators, and how they’re rolling out globally
- The future of OTAs, trust and discovery – from filter-based search (“Miami, Dec 23–Jan 1, max $600/night…”) to open-text intent (“I want a 2-hour flight, kid-friendly activities within walking distance, ocean view, pet-friendly”) – and how LLMs will sit between guests and inventory
We also cover Boom’s recent $13M Series A, backed by heavyweights including the former CEO of Hilton, major real-estate families, and top vertical SaaS founders—and why combining deep ops knowledge with frontier AI talent is their core edge.
If you:
- Run a vacation rental management company (50+ doors and up)
- Work at a PMS, channel manager, or OTA and want to see where the puck is headed
- Are thinking about how agentic AI will reshape operations, distribution, and guest experience
…this episode is a masterclass in where vacation rentals + AI are going next.
Guest: Shahar – Founder, Boom (AI-native PMS / operating system for vacation rentals)Connect with him on LinkedIn
If you got value from this conversation:
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- Share it with someone in your network who manages properties or builds tools for them
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