When AI Gets Personal: Hostaway Wins a Silver Stevie® for Customer Service

AI is everywhere right now. It’s promising lightning-fast answers using automation shortcuts, and maybe even a few more hours of sleep.

But here’s the thing people don’t talk about enough:

AI only works when it helps humans do their jobs better.

That’s why we’re proud to share that Hostaway has been named Silver Stevie® Award Winner for AI and Tech-Focused Customer Service Team of the Year.

Yes, it’s a big deal.

And yes, it says a lot about how we build technology and how we show up for our customers.

AI that supports people (not the other way around)

Hostaway was built for professional short-term rental operators juggling a hundred moving parts at once: bookings, guests, owners, platforms, pricing, and problems.

Our AI-forward platform helps automate the crazy day-to-day, like up to 93% of guest messaging, bringing insights forward faster and keeping teams focused.

But none of that works without exceptional human support behind it.

Our Customer Service team is not just answering tickets. They’re helping operators scale their business by acting as an extension of their team.  

We’ve all been there. You’re stuck in a loop with a bot that doesn't understand the word "emergency." Or waiting on a human who seems to have forgotten you exist.

But at Hostaway, we decided a long time ago that wasn’t good enough.

This Silver Stevie recognizes how Hostaway balances advanced technology paired with deeply human service.

“We use AI to remove friction and help us move faster, but always in service of better human conversations,” said Phil Hodges, VP of Customer Onboarding and Technical Support. “It allows us to spot trends sooner, support customers more consistently, and scale without losing the personal touch that customer success depends on. Seeing this work recognized at a global level is incredibly validating; not just for the technology itself, but for the way our team uses it to make our users’ lives genuinely easier every day.”

Why this recognition means more than the trophy

Industry awards are proof that what we’re building at Hostaway is working. Independent judges. Cutthroat criteria. Real competition.

For us, this win means our operators are feeling the difference when things get busy.

This is the part worth celebrating.

For our customers, that means reassurance.

For our team, it means recognition.

For Hostaway, it reinforces something we’ve believed all along. Great hospitality software should feel powerful and personal at the same time.

Built for operators. Backed by people.

From AI-powered automation to real humans who know the product inside and out, Hostaway’s approach to customer service is part of our product.

This award reflects the thousands of conversations, quick problem-solves, late-night saves, and proactive check-ins that happen every day behind the scenes.

And we’re just getting started.

Because the future of short-term rental tech is software that has your back.

We’re going to keep pushing the boundaries of what AI can do for the short-term rental industry, ensuring that Hostaway remains the smartest (and friendliest) tool in your tech stack.

At the end of the day, your success is our favorite award.

Want to see our award-winning service in action? Book a demo and let’s grow your business together.