What a Skift IDEA Awards Judge Is Looking for in Short-Term Rentals

Rena Pacheco-Theard co-built Boutiq with first-hand knowledge of the host role. Before their years of building revenue management, her team operated properties: they learned through hard-earned experience why STR solutions work or fail when you are the one responsible for occupancy. As a Skift IDEA Awards judge, she brings that lens to every entry: not whether an idea reads well, but whether it overcomes an obstacle that operators actually face.

Skift: What is one initiative or approach you’re most proud of that has positively impacted your business or the guest experience your partners can offer?

Rena: At Boutiq, we stay super-close to the host. We have been the host. We have property managers, and we have operated, so we bring an understanding of that role and its complexity and stresses to everything we do. We understand the problems, because we are authentic and we understand the industry in a way you simply cannot if you have not been an operator at scale. 

Skift: How are culture and community shaping traveler decisions, and how do you factor that in when assessing a property?

Rena: The reality is that there are a lot of choices right now. Oftentimes, a hotel can actually fit the needs of a group just as well as a full residence. What that means is you have to stand out in a very crowded marketplace. You have more search tools than ever before, and people have upped their game.

What makes you truly stand out in a crowded marketplace is the hyper-local—what you’re doing, how you’re talking about it, how the place is furnished—being as local as you can and making somebody feel like they are authentically in that community. What amenities do you have that set you apart? How do you describe your property in a way that presents a memory-making opportunity as a value proposition? Some travelers are certainly deciding on price, but if you’re going to earn the best return in this market, you can’t just be competing on price; you have to be competing on value.

Recently, we took a trip to evaluate different short-term rental platforms and direct booking sites. We went to a lodge for the historic fishing magazine, Field and Stream, in Bozeman, Montana. It’s cool, because it makes you feel like you’re in nature, in a place that understands the community you’re staying in and has invested in those community features, like fire pits, kayaks, or green common spaces. You pair that with local decor, and you’re in Bozeman, Montana and nowhere else. That is critical from a pricing perspective, because all of those pieces go together to create the value a traveler considers money well spent. The different investments and the way you set yourself apart with these features all contribute to pricing and booking velocity. That is what earns the best return, and that is what I look for.

What AI Is Changing

Skift: What is one insight about data, content, or platform management that short-term rental operators should be paying close attention to right now?

Rena:  I’m not the first person to say this, but we are still scratching the surface when it comes to AI search for travel. People are using more and more AI-augmented search tools and platforms, and even just the technology component of how images are rendered, how data is rendered and how scrapable it all is for AI search, all represents a very interesting opportunity for direct bookings. What are the different metrics of trust that you can put on your direct-booking website to give someone the confidence to book with you rather than a booking platform? How are you able to bridge that trust and confidence gap so that they purchase directly at a better price when they could pay a little more to use a trusted platform?

If you have the right inventory, and it is well-described, there is more of an opportunity now to show up in traveler searches than ever before. That is huge, and it has the potential to shift the share of bookings that go on platforms versus direct bookings. The platforms are aware of what’s happening, and I would foresee an opportunity for those platform fees to potentially become a little bit more competitive as travelers have more options that are surfacing and direct bookings, potentially, gain greater market share. 

AI surfaces a property, but there’s more to a booking

Rena: It’s not all down to convincing the AI; you also have to convince the traveler. AI will surface the results for a business that meets the traveler’s criteria and has a great price, but that traveler is going to click on those links, look at those photos, and they are going to be the ones that ultimately decide if it’s something they want to book.

You can show reviews on your page, but people might think you cherry-pick the reviews that are presented, but if you’ve got a feed of the reviews from other sites or some way of demonstrating the performance of your property across trusted platforms, and you’ve shared your story—who you are, where you’re located, what your history is and why you’re in this business, that you’re clean and trustworthy, then travelers will feel safe enough to book. So the AI search finds these initial parameters of what fits the bill, direct booking sites can fit the bill, and then it’s up to the traveler to actually decide if they feel confident enough to book. 

The Operator’s Reality

Skift: What trends do you think will define the next phase of short-term rentals and hospitality tech, and which ones are you most focused on?

Rena: For years, people keep talking about consolidation, that the short-term rental industry is going to do the same thing that the hotel industry did. There are certainly signs of that. There are some operators scooping up more regional players and trying to create a national brand, but the reality is I haven’t seen as much consolidation or it certainly isn’t happening as fast as people predicted. I actually keep seeing new entrants into the market, and it’s solving point solutions to specific problems rather than creating consolidation. 

The types of consolidation that I have seen are at the property management system level. Property management systems used to be calendar-syncing availability, distributing your listings, and maybe using a channel manager for communications. Now, they do so much more. The top property management systems offer their own pricing and many different tools, and I guess the question for operators is, do they want their PMS to be their everything? Do they think the property management system can be the best at everything that it does—whether they’re providing the accounting, the pricing, housekeeping, vendor management, what have you—or is there still space for the independent operators to do it best?

Skift: You have built and led a short-term rental AI/ML revenue management business in an evolving and competitive market. What is one lesson that has stayed with you?

Rena: The truth over all of these years is that there’s constant change, and you’ve got to understand the interest. Whether it’s interest rates or real estate prices, there’s a lot changing, and you have to look ahead and not be reactive. Understanding the interest means you have to be very clear about what motivates humans, because humans are at the end of any of these stakeholders that we’re talking about. I think that’s the way I approach this industry after so many years is really understanding what motivates someone and their likelihood to take different actions, whether it’s purchase decisions, or guests’ liability risks, you have to understand how everyone is evaluating the situation in order to appropriately plan, prepare, and respond. 

The Owner Stressors

I call it the fracking of the host. The host sits between the owner, who wants more, and the guest, who wants to pay less, so they’re fundamentally and forever at odds. And there are so many expectations in terms of regulation, home care, vendor management, revenue management, listing optimization. So many people want a piece of that pie, and expectations keep rising. So finding out what your sweet spot is—because you can’t be everything to everyone—and staying close to understand where the industry is going, where those interests are changing is essential. You stay relevant, you stay helpful, and you stay at that bleeding edge. 

Skift: Where do you see the biggest opportunity for AI or tech to make a real difference for guests, for your team, or for owners?

Rena: When it comes to integrating new technology, there’s excitement about the promise of what it is going to do, and there is also nervousness. Operators worry it will be complex, it will be just adding something to their plates rather than taking something off, and it may take away human jobs. I believe technology will ultimately free up humans to do more of what a human does best. At their core, the short-term rental industry and the hospitality industry are human. They are connection-based. It’s authentic. It’s about memory-making, and it’s very real. Technology at its best does the things that the human may not have time or be best-equipped for so that the human is freed up to do those things for hospitality that a human does best, making it so you can talk to a real person and have authentic interactions. 

Skift: What is driving Boutiq’s next phase of growth, and how are you positioning yourself to lead in an increasingly competitive short-term rental landscape?

Rena: Our next phase of growth is really driven by focus. I mentioned that we understand the host because we’ve been operating, but we are not going to keep operating at Boutiq. We have earned our stripes there. That was not easy. But we are going to focus purely on the revenue-management and technology side, and that focus will allow us to better serve our clients and to focus on our next phase.

We’ve been heads-down building out the technology, understanding all of those perspectives, getting the data on how we do what we do and working to qualify that impact. It’s time for us to turn on the growth engine, and it’s time to connect more. We’ll probably go to more industry events, driven by that focus that allows us to put our heads up and look around and find out who we should be partnering with, what we should be building together, and how we’re going to work to make this industry even better. It’s an exciting period of time. 

It’s bittersweet, because we became used to being an operator and identifying partly as an operator, and it feels weird to hang that up, but that’s change. Change feels weird, but it’s what you do. And we’re going to keep learning and evolving, so I’m excited for the next phase. The focus that we’ll get from making that change is going to really benefit us and the folks we serve. 

Skift IDEA Awards

Rena joins the judging panel for the 2026 Skift IDEA Awards, which recognize the most innovative ideas across travel. Winning signals that an idea has met the standard of someone who has operated at the problem’s center, not from its periphery. Get your entry in front of the judges today.