Robots, AI Employees and Dynamic Travel: What Gilad Berenstein Is Bringing to Skift Data + AI Summit

A startup operator turned investor with deep roots in travel innovation, Gilad has built a career by seeing around corners, and at this year’s Skift Data + AI Summit, he’s set to share what’s coming next.

Brook Bay Capital invests in the future of travel, technology, and data, with a sharp focus on where automation and personalization converge. Gilad’s experience gives him a unique vantage point on how data and AI are reshaping not only how we travel but what we even consider a travel product.

Ahead of the summit, we caught up with Gilad Berenstein for a fast-paced Q&A to unpack the most disruptive trends he’s tracking.

“Oh, so many,” Gilad said, “but a few key ones include robotics, AI employees, travel clubs, and the human connection.”

“Robots are coming to a hotel near you and soon! The price of manufacturing is dropping, the ease of managing them is growing, and the number of founders focused on this space has exploded.” According to Gilad, while China has already embraced this technology, “I think the next 12 months we will see this deployment come to the US.”

Next, he drew a sharp distinction in how we think about AI workers: “Not Aigents that need a new set of rails, but AI Employees who are ready for primetime right now,” he emphasized. These are not simple bots, but operationally capable digital team members ready to plug into real workflows.

On the topic of personalization and brand affinity, he highlighted the rise of AI-first travel agencies and clubs, calling them “a massive proliferation” and “very exciting for the industry and for travelers.”

And amid the tech boom, Gilad insists the human connection is more essential than ever.

“In a world of ubiquitous AI and technology, a focus on the human connection between traveler and brand is perhaps the best differentiator.”

“Dynamic Products,” Gilad answered without hesitation.

He explained: “Over the past 30 years, we have seen enormous innovation in the way we market and sell travel products… but we have seen nearly zero innovation in the things we sell.” From flights and beds to dinner reservations, Gilad pointed out that travel inventory has remained fundamentally unchanged.

“By combining AI, new hard product offerings, and drop shipment providers, we will enter an era of Dynamic Products where each product is dynamically created for a given customer,” he said. The outcome? “A true win-win-win: better, more personal trips, increased margin for travel sellers, and a more sustainable industry for us all.”

Gilad pointed to an often overlooked part of the hospitality ecosystem: the back of house.

“A few months ago, I wrote a short essay titled Back of House Ozempic,” he shared. “This is a huge opportunity in hospitality and one most founders are ignoring—and probably not qualified for.”

He emphasized how the majority of startups are focused on guest-facing experiences like trip planning and marketing. “When I speak with hotel operators, they tell me that for every 100 startups that reach out about marketing, trip planning, recommendations, etc., they maybe get one startup focused on the back of the house.”

That’s where he sees the real opportunity: “Housekeeping, laundry, the kitchen, the back office are all ignored; partially because most tech founders have not worked in many laundry rooms.”

With labor shortages and rising costs affecting the industry, Gilad concluded, “Combining the impacts of labor shortages, wage inflation, and AI is a win-win opportunity!”

While the buzz often centers on guest-facing tech, Gilad is urging founders and operators alike to look deeper into the guts of the industry, into overlooked workflows, and into the spaces where AI could quietly revolutionize everything.

As the Skift Data + AI Summit approaches, one thing is clear: travel won’t evolve by accident. It will be shaped by those bold enough to question the fundamentals and build what comes next.

Continue the conversation with Gilad Berenstein and other leaders at Skift Data + AI Summit and discover what the future of travel looks like before it arrives.

June 4, 2025 - NEW YORK CITY