AI assist
Earlier this month, technology entrepreneur Matt Shumer published a widely circulated essay titled “Something Big Is Happening.” According to an article from Modern Engineering Marvels, “A long essay by 26-year-old founder and investor Matt Shumer, called “Something Big is Coming”, went viral on X, getting more than 60 million views on the site.”
In it, he compared today’s artificial intelligence moment to February 2020 — that uneasy stretch when most people sensed distant rumblings but had no idea how quickly daily life would change. None of us were sure what Covid might mean. I, for one, bought a dog.
But the gist of his central message from this example was blunt: the shift is already underway. The only question is who will pay attention in time. Janice Passos, of Eteriz. with AI expertise in the timeshare resort business, says, “In this moment, we have a pivotal choice: be proactive and shape what’s coming or be reactive and manage the consequences.”
Like the emergence of the Internet, this is a strategic issue that touches operations, sales, marketing, finance, owner communications, compliance, training, and long-term workforce planning. It will touch everything – both in your business and your personal life. The other day, I uploaded my monthly insurance bills into ChatGPT asking for advice on a better provider. I saved hundreds!
Just as online booking reshaped hospitality in the early 2000s, AI is poised to reshape knowledge work in the late 2020s. The difference is speed.
The tech world often introduces ‘the next world-shaking thing.” Think of the plethora of apps that are being introduced every day for example. In hospitality, we have seen technology waves before — online booking, channel management systems, CRM platforms, dynamic pricing, digital marketing automation. Each required adaptation. Each reshaped staffing and workflows.
What makes AI different is not that it automates a single task. It does…. It automates cognitive work — reading, summarizing, analyzing, drafting, forecasting, coding, communicating. But it can do so much more. It can organize data to use in marketing at lightening speed. AI draft legal arguments, build financial models, generate complex code, and conduct analyses of just about anything.
It’s a force multiplier for human judgment, not just a substitute for execution.
Let’s bring this down to ground level. In a typical timeshare or vacation ownership operation, consider how much work involves:
All of these tasks happen on a screen. All of them involve structured information. All of them are candidates for AI augmentation.
This does not mean replacing professionals. It means redefining roles. A general manager who once spent three days assembling a board packet may now generate a first draft in an hour and devote more time to interpretation and strategy. A marketing director can test multiple campaign variations before launch. An HOA administrator can quickly identify trends in owner complaints before they escalate.
Those who understand the tools will become exponentially more productive. Those who ignore them risk falling behind competitors who do not. But it’s going to require constant vigilance. In his article Shumer says, “The future is being shaped by a remarkably small number of people: a few hundred researchers at a handful of companies… OpenAI, Anthropic, Google DeepMind, and a few others. A single training run, managed by a small team over a few months, can produce an AI system that shifts the entire trajectory of the technology. Most of us who work in AI are building on top of foundations we didn’t lay. We’re watching this unfold the same as you… we just happen to be close enough to feel the ground shake first.
“But it’s time now. Not in an “\’eventually we should talk about this’ way. In a ‘this is happening right now and I need you to understand it’ way.”
The most important takeaway from Shumer’s essay for me was a sense of urgency. He argues that the window for early adopters is still open — but not for long. The same applies to our industry.
Resort executives who experiment with AI now will shape internal policies, set ethical guardrails, and develop institutional knowledge before reactive adoption becomes necessary. They will ask:
This is not theoretical. Here [courtesy of ChatGPT] are immediate, practical use cases for resort professionals:
Related – 5 AI Hacks Every Executive Should Try
Related – How AI Makes Me a Better Leader
These tools are not perfect. They require oversight. But they are improving at a pace few anticipated.
“AI won’t redefine hospitality’s heart, but it will absolutely redefine its engine,” says Passos. Perhaps the greatest challenge is not technical but cultural. Many professionals pride themselves on experience — and rightly so. Institutional knowledge, relationship capital, and judgment are irreplaceable assets in vacation ownership.
But AI does not diminish expertise. It amplifies it.
A seasoned resort manager using AI as an analytical assistant can surface insights faster than a competitor relying solely on manual review. A board advisor can generate comparative research before a meeting or call. Obviously, the competitive advantage lies not in resisting the tool but in mastering it.
Shumer references projections suggesting substantial disruption to entry-level white-collar roles. While timelines are debated, one reality is clear: job descriptions will evolve.
ChatGPT says “For resorts, this means:
If all of this raises your eyebrows about various traps, you’re not alone. ChatGPT mentioned the following concerns:
Resort professionals operate in a fiduciary environment. Boards and management companies must proceed thoughtfully. But thoughtful does not mean passive. Resort companies will need to set up guardrails, much like we’ve all had to regulate how email communications have certain rules.
The responsible path forward is experimentation within guardrails — secure environments, anonymized data, internal review protocols, and clear usage policies.
The vacation ownership industry has always been relationship-driven. That will not change. Owners still expect human connection. They expect accountability. They expect leadership.
AI cannot attend an annual meeting and look an owner in the eye. It cannot build trust over decades.
What it can do is eliminate administrative friction, accelerate analysis, and free leaders to focus on what truly differentiates successful resorts: service, communication, and strategic foresight. The early adopters in our industry will not be the ones who replace staff indiscriminately. They will be the ones who empower staff with better tools.
If you have not seriously explored AI in the past six months, now is the time.
Not casually. Not as a novelty. More advice from ChatGPT suggests dedicating structured time to:
We suggest you encourage your staff and cohorts to begin using AI whenever possible. Bring it up at the next leadership meeting. Discuss implications at the board level. Ask vendors how they are integrating AI into their services.
This is not hype. It is infrastructure.
Shumer’s essay frames this moment as historic — not just for business but for society. Whether one agrees with the most dramatic forecasts, the directional shift is undeniable.
For resort professionals, the choice is straightforward: Observe from the sidelines and react later [insert frowny emoji]. Or engage early, learn deliberately, and shape how this technology serves owners, boards, and guests. Our industry has weathered recessions, regulatory shifts, pandemics, and market cycles. Adaptation is part of our DNA.
Like Shumer says, “Something big is happening.” The leaders who treat this year as a strategic turning point — rather than a ‘business as usual’ — will be the ones best positioned when the next phase arrives.
Sharon Scott Wilson, RRP, operates Resort Trades Media Group, publishers of Resort Trades magazine and other media, delivered nationwide at no charge to timeshare resort professionals. Subscribe at https://resorttrades.com/subscribe.
Travel + Leisure Co. (NYSE:TNL), a leading leisure travel company, today announced plans for a…
Somewhere in your organization right now, someone who should be solving a real problem is…
Abstract: Company leave policies must comply with a growing patchwork of overlapping federal, state and…
The past twelve months have marked one of the most consequential periods in the history…
When you hear the title Meatballs & Mindset, you might expect a cookbook, a family…
Sena Hospitality Design Inc., an Orlando-based licensed interior design firm specializing in resorts, has been…