How AI can send offers to your guests

This week, we're looking into something that's reshaping how the best hosts operate: artificial intelligence.

Our guest is Dragos Diac, a hospitality innovator helping short-term rental operators and boutique hoteliers put AI to work on real problems.

He founded the first AI autopilot for short-term rentals in early 2023 and has worked with solo hosts and large operators alike.

His focus: turning complex “tech stuff” into practical wins, automating messaging, streamlining operations, and elevating the guest experience.

A frequent speaker and contributor at industry events and publications, Dragos specializes in hands-on, autonomous AI solutions for hospitality.

If you've ever wondered what AI can actually do for your rental, this one's for you. I did a demo call of Dragos's product, and I was impressed with what he and his team have created.

Anastasia: What pulled you into the AI space within hospitality?

Dragos: I always saw myself as a techie, trying the latest technologies whenever something new came out.

Before hospitality I was managing a data science agency here in London and when ChatGPT launched in late 2022, I was very curious to find out whether this new technology could actually automate communications with real people.

I was fully aware that messaging is really important to the guest experience, but it can also be very repetitive. I thought if we could find a way to automate just the repetitive part and let property managers handle the decisions that require judgement or a personal touch, that would be genuinely valuable.

So it started more as an experiment for me, really. I wanted to see if this new technology could support property managers to become more efficient with their time. The idea grew from there as we discovered what was actually possible and what the real challenges were in making it work safely.

Anastasia: What are the biggest inefficiencies or gaps you see in how most hosts run their operations?

Dragos: The biggest issue I see is that guest communication eats up far more time than it should. What happens is that as you grow, you either hire more people just to keep up with messages, or you start responding slower and the guest experience suffers.

Either way, you're stuck in a loop where routine communication becomes a bottleneck that prevents you from focusing on the things that actually grow your business, like building owner relationships, improving properties, or taking on new listings.

The gap is that most operators don't have a good way to handle the routine stuff automatically whilst still maintaining quality and knowing when something needs their personal attention. That's where AI can actually make a meaningful difference.

Anastasia: Can you give us an example of someone you’ve helped apply AI in their business?

Dragos: One of our first clients was this couple Leo and Millie, a family-run business managing 25 listings. When we talked about their operation, what stood out was how guest messaging had become a constant interruption to their family life. The messages were repetitive, mostly the same questions over and over, but they still needed responses.

Once they saw a demo, it clicked for them. They didn't need AI to grow the business. For them it was mostly so they could have a more normal life with fewer interruptions.

Their AI now handles the routine questions automatically, which means they can sit down for dinner without checking their phones constantly or take a day off without worrying about guests.

What surprised them was the business impact.

Response times improved immediately, which led to more bookings.

The AI also started proactively sending special offers to guests about extending their stays, something they'd rarely had time to do manually. That alone brought in additional revenue they weren't capturing before.

So whilst they came to us looking for time back, they ended up with both that and a more profitable operation.

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Anastasia: Many people think AI is just chatbots or guest replies. But you’ve gone much further. What are a few creative or overlooked ways to use it?

Dragos: What most people don't realise is that these AIs can actually think through complex situations and follow detailed instructions. It's nothing like the templated responses from the past.

Early check-in requests are a good example.

There's a lot to consider: Is there a same-day checkout? What time did the guest ask for? When did they ask? Do we need to check with housekeeping first?

Check out the logic:

​https://www.aeve.ai/images/Diagram.svg​

Figuring out what needs to be done, taking all these dimensions can be draining for any normal person and sometimes leads to errors that impact the guests.

Our AI agent, Eve, was built to handle the routine but also more complex cases like these.

This is what allows us to automate as much as 80-90% of all guest communications. She knows when to ask for more details or when she needs to wait for housekeeping before saying anything.

Knowing when not to respond is actually super important. A guest complaining about cleanliness, asking for a refund, or reporting a serious maintenance problem should never get an automated response. We've seen other AIs mess this up but our system escalates these straight away so a real person can handle them.

Anastasia: What tools or platforms are you currently most excited about?

Dragos: Besides our work on the AI autopilot, I'm really excited about AI coding tools. I use them heavily to build custom solutions for STR operators, and they've completely changed what's possible with a small team.

What used to take weeks of development work can now happen in days. When an operator comes to us with a specific need, something custom to their workflow, we can prototype it, test it, and deploy it very quickly.

We're not constrained by development capacity the way we used to be.

Someone might need a custom agent for coordinating with property owners, or a knowledge system that pulls answers from their specific operational files.

We can build these things at a speed that wasn't possible even a year ago.

Smaller, focused teams can now compete with much larger operations because the tools have levelled the playing field in a significant way.

Anastasia: For someone who isn’t technical, AI can feel intimidating. What’s the first step you’d suggest for a total beginner?

Dragos: Just start using ChatGPT for more things in your day-to-day work. When you need to figure something out, give it the context and see how it handles it.

Maybe you need help writing a difficult email to a guest, or you're not sure how to respond to a property owner about something. Give the AI the details and see what it suggests. Try asking it to brainstorm solutions for an operational problem you're facing.

The more you use it, the more you'll understand what it's good at and where it falls short.

What happens is you start to develop an intuition for how these tools think and where they can actually help. You don't need to understand the technology behind it. You just need to experiment with it in situations where the stakes are low and you can review the output before using it.

Once you're comfortable with that, you'll have a much better sense of where AI could fit into your operation and what problems it might actually solve for you.

Anastasia: The space is moving fast. What do you think is coming that hosts should be preparing for?

Dragos: The bigger picture is that competition is intensifying across the industry. More operators are entering the market, costs are rising, and guests expect better service at the same or lower prices. The margins are getting tighter, and the operational pressures aren't going away.

What's coming is that the operators who adopt technology to handle routine work will have a significant advantage over those who don't.

Hosts should be thinking about how their team roles will need to shift. As AI handles more routine tasks, the valuable skills become judgment, relationship building, and quality oversight.

Someone who understands guest needs and owner concerns deeply will be more important than someone who's simply fast at responding to messages.

For smaller operators, this might be what allows you to grow without burning out.

For larger operations, it probably means restructuring so people focus on work that genuinely requires human attention. The operators who will do well are the ones who see automation as a way to stay competitive and elevate what their teams do, not just as a cost-cutting exercise. ​
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Anastasia: If a host could only take one thing away from this conversation, what should it be?

Dragos: The one thing I'd want hosts to take away is that you need to start experimenting with this technology sooner rather than later. You don't need to automate everything overnight, but you should be learning how these tools work and where they fit into your operation.

The operators who wait too long will find themselves competing against others who are running more efficiently, responding faster, and delivering better experiences at lower costs.

Make the effort now as it will allow you to stay competitive in an industry where the pressures are only increasing.

Start small, learn what works, and think about how your operation needs to evolve. The gap between those who adapt and those who don't is going to widen quickly.

Anastasia: Thank you! That was very helpful.

Dragos: My pleasure!

If you want to learn more about them, check out their website. If you decide to do a demo, ask them to show you how their AI tool can send automated messages with offers for adjacent days.

That was one of the most impressive features for me.

That's all for today,

Till next week, dear readers.