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The short-term rental industry faces a paradox: while professional operators deliver exceptional guest experiences and contribute meaningfully to local economies, the public narrative remains dominated by stories of housing shortages, party houses, and tax avoidance. This is a fundamental communication failure that affects everything from regulation to revenue.
Jessica Gillingham, founder of Abode Worldwide and author of Tech-Enabled Hospitality, has spent nearly a decade helping hospitality tech companies tell their stories. In a recent conversation, she explained why the industry struggles to communicate its value and what operators and tech companies can do about it.
Jessica's path to becoming one of the industry's leading voices wasn't linear. She started in Canadian travel, running her own platform selling cottage holidays to British guests right as Airbnb was emerging in urban markets. At the same time, she worked in deep tech PR, learning to communicate complex semiconductor solutions.
"I sort of learned two things at the same time," Jessica explains. "One was around travel and hospitality. The other, which was diametrically opposed, was all about deep tech and how to communicate very complex technology solutions."
When investment started flooding into short-term rental tech, Jessica found herself uniquely positioned. She could translate technical innovation for hospitality operators, and explain hospitality challenges to tech founders. It was, as she puts it, "a lucky accident."
But those lucky accidents tend to happen when you combine skills that aren't commonly paired. The convergence of her expertise arrived at exactly the right moment: when the industry needed someone who could speak both languages.
The industry's communication challenges operate on multiple levels:
The public hears about housing shortages and disruptive guests. They don't hear about the small business owners, the economic contribution to rural communities, or the fact that professional short-term rentals often solve problems rather than create them.
"The industry hasn't been able to communicate the value, the positives, the actual real impact that professional short-term rentals bring to communities, to economies, to tourism in an area," Jessica notes.
Some associations are making progress. Portugal's ALEP ran grassroots campaigns highlighting the real people behind property management. Not anonymous platforms, but small business owners and families. The strategy works because people relate to people, not corporations.
On the B2B side, many hospitality tech companies sound identical. Generic value propositions create a vanilla landscape where buyers can't distinguish between products.
"It's not always clear what category they're in or what's unique about a particular company or solution," Jessica observes.
As the industry evolves, with flexible living, branded residences, and hybrid hospitality models, the lines between categories blur. If you can't clearly articulate what you are and who you serve, you become invisible. This matters more than ever as AI-powered search changes how people discover accommodation and solutions.
When Jessica interviewed 38 senior leaders across hospitality for her book, she expected to hear about technology. Instead, she heard about people.
"Everybody I spoke to really looked at it from quite a human perspective — what's the impact of whatever technology we use on either the operator and their team, or the guest," she says. "A leading phrase that all the leaders said is that the future of hospitality is hospitality."
The technology enables better service, but it doesn't replace the fundamental human experience. Even in an era of AI agents and autonomous properties, the core value proposition remains unchanged: providing an experience, a feeling, great service.
Three other themes emerged from her research:
The short-term rental industry is ahead on innovation. Distributed properties, unique units, and multiple owners are all challenges that don't exist in traditional hotels. Necessity drove innovation, and operators who came from property management built solutions for their own problems.
But hotels lead in other areas:
The gap isn't insurmountable. But it requires operators to think differently about their business — less as property management, more as hospitality.
Search is changing. People don't type queries into Google and choose from 10 blue links anymore. They ask ChatGPT or Claude for recommendations and get answers.
"When we search on LLMs, we get provided an answer," Jessica explains. "It's not choice. It's actually an answer. And we're not given all the other opportunities that we might've looked at to do that due diligence against."
This changes everything for both operators and tech companies.
If you're not clear about what category you're in, what you offer, and who you serve, you won't appear in those recommendations. The LLM will either skip you entirely or put you in the wrong bucket.
Buyers are doing their due diligence elsewhere now. By the time they reach your website, they've already decided, or narrowed it down to you and one competitor. They're not still figuring out what they need. They're confirming you're the right choice.
This means:
The operators and companies that figure this out first will capture a disproportionate share of traffic. We're likely seeing the beginning of a concentration effect.
One of the most significant trends reshaping hospitality is the blending of residential and short-stay models. Jessica calls it "flexible living" though the term doesn't have a universal definition yet.
In some markets, it means co-living. In others, it describes buildings that house both long-term tenants and short-stay guests. Student accommodation becomes short let in summer. Branded residences operate like hotels. Build-to-rent properties add hospitality services.
"What we're seeing is operators and asset classes looking at customers differently than just a siloed group," Jessica notes.
Several forces drive this convergence:
This creates opportunities for short-term rental operators who understand how to deliver experience at scale. Asset owners need people who know how to handle turnovers, manage reviews, optimize pricing, and create memorable stays.
"There's an opportunity for operators to go in and operate in different building classes," Jessica says. "It can only be a good thing for the short-term rental sector, and particularly operators that see it as an opportunity, not as competition or a threat."
Abode Worldwide's annual hospitality tech investment index tracked over $1 billion in public deals over the last year. The pattern is clear: capital is concentrating in the operational layer.
Roughly $400 million went into property management systems. Other operational software captured most of the rest. Point solutions received less attention.
This signals consolidation. The platforms are getting broader. The cost of developing software has collapsed, which means the natural equilibrium shifts toward fewer, more comprehensive solutions.
We've already seen this with PMSs through years of mergers and acquisitions. Now a third wave is coming: companies that previously specialized in narrow functions will either compete directly with platforms or form tighter partnerships that lead to consolidation.
The ecosystem will likely become less diverse, but the surviving platforms will be more capable.
Abode Worldwide runs fully remote. After nearly 10 years, Jessica has learned that remote culture doesn't happen by accident. It requires deliberate investment.
Her team meets quarterly for in-person days. They attend industry events together. Education is a core value — team members go to conferences as part of their professional development, not as a perk.
They use technology to stay connected. They even have a "culture club" where team members organize activities like book clubs, active challenges, virtual hangouts.
"I don't think you can have a remote team that is very successful without putting quite a lot of thought and effort into it," Jessica says.
The foundation is clarity, one of Abode's four core values. Clear communication, clear expectations, clear feedback. In a remote environment, you can't rely on proximity to fill in the gaps.
And authenticity matters more than perfection. "One of the things about leadership that I've worked out is I have to show up as myself," Jessica reflects. "It's really important that I show up authentically and with integrity."
The industry's reputation problem is a communication problem: Professional short-term rentals contribute to local economies and provide quality hospitality, but the public narrative focuses on housing shortages and party houses. Associations in Portugal and other markets are making progress by highlighting the real people behind property management.
Tech companies struggle with differentiation: Generic messaging makes it impossible for buyers to distinguish between solutions. As LLM-powered search becomes dominant, clarity about category and value proposition isn't optional but existential.
The future of hospitality is still hospitality: Despite rapid technological advancement, industry leaders consistently emphasize the human element. Technology enables better service, but the core value remains the experience you create for guests and teams.
Hotels lead on personalization and brand: While short-term rentals innovate faster on operations, hotels have more developed guest relationships, loyalty programs, and brand consistency. This gap represents an opportunity for operators willing to invest in direct booking strategies.
Flexible living creates opportunities: The convergence of residential and hospitality models is a chance for operators to apply their expertise in new asset classes. Capital is flowing toward buildings that can serve multiple guest types and stay durations.
Search is changing everything: LLMs provide answers, not options. If your messaging isn't clear and consistent across channels, you won't appear in recommendations. Buyers complete their research before they reach your website.
Remote culture requires investment: Distributed teams don't build culture accidentally. It takes quarterly meetups, shared learning experiences, deliberate communication tools, and leadership that shows up authentically.
The short-term rental industry stands at an inflection point. Regulation, reputation, and technology are all shifting simultaneously. The operators and companies that thrive won't be the ones with the best properties or the most features. They'll be the ones who can clearly articulate their value.
That means understanding your category. Knowing who you serve. Communicating consistently. And recognizing that while technology enables everything, hospitality remains fundamentally human.
As Jessica's research revealed, the leaders who understand this don't talk about empowering platforms or seamless solutions. They talk about the guest who didn't realize how loud they were, the small business owner who needed proof for an insurance claim, the family who found the perfect place to stay.
The future of hospitality is hospitality. The companies that remember this, and can communicate it clearly, will be the ones that shape what comes next.
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