The Vacation Rental Company Deflecting 60% of Guest Inquiries With AI

Arun Nagarajan, Chief Product and Technology Officer at Evolve, has spent two years moving AI from pilot to infrastructure across one of the fastest-growing hybrid vacation rental companies in the U.S. 

Evolve owners now earn 18% more revenue and book 9% more nights than the market average. That’s what execution, rather than experimentation, looks like on the P&L.

At Skift Data + AI Summit 2026, Nagarajan will get into what actually changes when an organization crosses that line.

What is the single most important factor for successfully scaling AI in travel operations?

“Fundamentally, AI at Evolve is about scaling impact for our customers — not AI for its own sake. We’re a hybrid vacation rental management company built on a model we’ve pioneered — one that gives owners something the industry hasn’t historically offered: unprecedented flexibility and high performance. And this hybrid model is perfectly structured to intercept AI.

We started in late 2024 using LLMs to accelerate listing builds and QA, getting owners to their first booking faster. In late 2025, we deployed AI for guest support on routine inquiries — and we’re now deflecting over 60% of those conversations without human intervention. In 2026, we’re using AI more broadly in engineering, revenue management, sales, and beyond.

The operating principle that ties all of it together: How do we add more value to the customer, faster? Sometimes that means doing something entirely differently. Sometimes it means accelerating something we were already doing. But the goal is always customer impact and the speed at which we deliver it.”

How do you approach measuring AI’s value?

“The why behind every AI investment is the same: Drive more value for our customers. And we measure the return on our investments through the P&L.

Over the last two and a half years, we’ve rebuilt our core tech stack to make our systems inspectable:

• How many owners reached out about a damage claim yesterday?
• How long did we take to respond?
• How many new bookings did we generate in a given market?
• How does that compare to last year?

Our instrumentation is what lets us connect AI investments directly to customer outcomes — and ultimately to the P&L. Because when customer outcomes move, everything moves. And they are moving: Evolve owners and operators earn 18% more revenue and book 9% more nights than the market average. That’s what happens when owner performance and Evolve’s performance are structurally aligned. The only way we win is if our owners win first, and AI is what’s pushing customer outcomes further, faster.”

What is your advice on balancing AI and human judgment?

“Humans need to be accountable — not AI. So put your highest-judgment people in charge of AI initiatives and have them own the audit and evaluation process. The right people working alongside AI will outperform either alone. And when mistakes happen as you scale, they’ll be the ones who can quickly detect, react, and improve. Give them the ownership, and they’ll thrive and deliver massive impact.“

What AI prediction would surprise the travel industry?

“There are going to be a lot more ways your customer will want to interact with your product or service, and the industry hasn’t fully reckoned with that yet. We’ve spent the last two decades building apps and websites for humans. We have yet to figure out how to make all of this work for agents. Your customer’s AI agent may want to talk to your company’s AI agent — but how does it find that agent, how do we call it back, and what language do they speak? We have a lot to solve here.

So my big prediction for the next 12–24 months: We have to switch from UX (user experience) to AX (agent experience).“

Hear Nagarajan at Skift Data + AI Summit

The next phase of travel AI belongs to companies connecting automation directly to revenue, operational performance, and customer outcomes. Nagarajan’s session at Skift Data + AI Summit this June is for the operators who’ve run the pilots and now have to decide what comes next.