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- Reinventing Hospitality with AI [Newsletter #88]
Reinventing Hospitality with AI [Newsletter #88]
From Business Needs to AI Execution
Hello, AI enthusiasts from around the world.
Welcome to this week's newsletter for the AI and the Future of Work podcast.
Millions of people travel every day with one goal in mind: a smooth, enjoyable experience.
Whether for business or leisure, travelers want less friction. AI promises to deliver exactly that by learning more about guests and anticipating their needs.
But there’s tension at the center of this promise: the more AI learns about you, the better it can serve you—so what happens when it learns too much?
In this week’s conversation, we explore how AI is becoming essential to success across the travel industry, from global brands to smaller operators. At the same time, we examine the responsibility that comes with it. AI brings efficiency and personalization, but it also demands strong security, thoughtful governance, and human oversight.
Let’s dive into this week’s highlights! 🚀
🎙️New podcast episode with Scott Strickland, Chief Commercial Officer at Wyndham Hotels and Resorts
It’s been a long trip. Your flight was delayed. You missed your connection. Hours pass in an airport lounge. Every seat on the next flight is taken.
You don’t want small talk. You don’t want friction. You just want your room key and a quiet place to rest before tomorrow’s meetings. But there’s a line at check-in.
Now imagine something different.
You step out of the taxi. Your phone confirms your room. The elevator opens. In less than a minute, you’re inside, door closed, shoes off. No desk. No waiting. No paperwork.
Scott Strickland believes this experience is within reach, and AI is the reason why.
Hospitality runs on data. Every trip generates signals, dates, destinations, preferences, loyalty history, transportation details, room requests.
Scott sees a future where AI connects those signals to remove friction across the entire journey. Small touches, like anticipating room preferences. Bigger shifts, like seamless check-in and check-out without standing in line.
This is only part of his vision as the Chief Commercial Officer of Wyndham Hotels & Resorts, a role he assumed in April 2024. Previously, he served as the Chief Information Officer (CIO) for Wyndham Hotel Group from 2017 to 2024.
In his conversation with PeopleReign CEO Dan Turchin, Scott explains how data and AI can make hospitality more adaptable for millions of guests each year. But there’s a boundary.
The more data companies collect, the closer they move toward what Scott calls “the creepy line”, the moment personalization starts to feel like surveillance.
In this conversation, we discuss this and much more:
AI must start with clear business outcomes. As Scott explains, the goal is simple: drive efficiency, increase revenue, or create entirely new businesses.
Wyndham began with just four focused use cases. They proved ROI first, then scaled what worked.
AI can remove friction across the guest journey, but hospitality remains a human business. Technology enhances the experience. People deliver it.
Security and privacy are not afterthoughts. They belong in the design process from day one.
Transparency with employees matters. When teams understand how AI is being used, they’re far more confident adopting it.
🎧 This week's episode of AI and the Future of Work, featuring Scott Strickland, CCO of Wyndham Hotels & Resorts, is now available.
Listen to the full episode to learn more about how both the hospitality industry and guests have moved the “creepy line,” because guests provide more data, but expect more in return, and how AI plays a crucial balancing role.
📖 AI Fun Fact Article
Will AI be the end of call centers? It depends on who you ask.
BBC journalist Jane Wakefield posed the question to ChatGPT. The answer was diplomatic. Humans and AI will work side by side.
Not everyone shares that optimism. Research firm Gartner predicts that by 2029, AI will autonomously resolve 80% of common customer service issues.
You can read more about this research here.
At the same time, 85% of customer service leaders are exploring, piloting, or deploying AI chatbots. Yet only 20% of those initiatives fully meet expectations.
Why the gap?
One key reason is training data. AI systems require large amounts of it, and that data is expensive and difficult to access.
These two factors alone increase costs, challenging the idea that AI is always the cheaper option.
That said, there are success stories. Salesforce reports that 94% of customers choose to interact with AI agents when given the option.
The company also claims a $100 million reduction in customer service costs. At the same time, Salesforce CEO Marc Benioff downplayed headlines suggesting that this led to 4,000 fewer jobs.
PeopleReign CEO Dan Turchin reminds us that service quality should drive innovation, not simply the desire to remove humans from the process. No one benefits when service experiences are degraded because technology has been awkwardly inserted.
When technology is truly superior to traditional human to human interaction, people will adopt it naturally. What we’re seeing now often feels forced, with profit motives driving behavior.
‘AI washing’—the overstatement of AI’s efficacy—is everywhere. Yet the technology still lags behind self-serving claims, like the 94% preference above by Salesforce.
The conversation also needs more nuance. Some service interactions are nearly deterministic and are strong candidates for automation:hings like tracking packages or checking the status of a ticket are ideal applications. Others, like troubleshooting technology or ordering custom goods, invite bad behavior by AI because they’re inherently complex, and training data is sparse for every permutation.
To avoid consumer backlash and cultural resistance to AI, now is the time for leaders to be especially cautious about what they say, how they qualify misleading predictions, and most importantly, how they exercise restraint.
Before rushing products to market that haven’t been safety tested. Every technology goes through this adoption cycle. In this case, the past is most certainly a prologue.
Listener Spotlight
Andrew in Boise, Idaho, is a photographer and entrepreneur. His favorite episode is #298 with Zapier CEO and co-founder Wade Foster, where Wade shares his journey from intern to building a $5 billion unicorn.
🎧 You can listen to that excellent episode here!
As always, we love hearing from you. Want to be featured in an upcoming episode or newsletter? Comment and share how you listen and which episode has stayed with you the most.
🏅 Celebrating a Top 20 AI Podcast Recognition
We’re excited to share that AI and The Future of Work has been recognized as one of the 20 Best Podcasts for AI by Interview Valet.
This recognition means a lot to us, reflecting the passion, curiosity, and expertise of our guests, our team, and everyone who tunes in to explore how AI is transforming the world of work.
Thank you, Interview Valet, for including us in this curated list of standout shows shaping the conversation around artificial intelligence and its impact today.

Worth A Read
We often hear that AI will reduce workload and eliminate repetitive tasks. That vision focuses on the outcome. The path to build it looks different.
Twelve-hour days. Limited weekends. Sustained pressure to ship faster than competitors. This defines the pace inside many AI startups.

Source: The Guardian
Startup culture has always demanded long hours. The current AI race intensifies that pressure. Teams compete for funding, talent, and market position in an environment that shifts quickly.
There is excitement around building new systems. But there is also concern about staying ahead in a volatile market.
How are founders and employees navigating that tension?
This article examines the work culture inside San Francisco’s AI startup ecosystem, where ambition, competition, and burnout often coexist.
Recommended Listening
To mark our February special compilation, we released a new episode of AI and the Future of Work exploring what it takes to build AI companies that endure.
Across industries and stages, each founder tackles a different piece of the same question:
How do you build something that lasts in the age of AI?
Featured perspectives:
Eric Olson, Co-Founder and CEO at Consensus
Richard White, Founder & CEO at Fathom.ai
Dmitry Shapiro, CEO of MindStudio
Daniel Marcous, Co-Founder, CTO & CPO at april
George Sivulka, Founder & CEO at Hebbia
📣 Share your Thoughts and Leave a Review!
We'd love to hear from you. Your feedback helps us improve and ensures we continue bringing valuable insights to our podcast community. 👇
Until next time, stay curious! 🤔
We want to keep you informed about the latest developments in AI. Here are a few stories from around the world worth reading:
One investor believes AI could lead to higher taxes on capital, while eliminating taxes for most workers. Here’s how he envisions scrapping taxes for 125 million people.
The European Parliament has blocked AI tools on lawmakers’ devices, sparking a broader debate about safety and governance. Here’s more.
One doctor is actively training AI to do her job, and she’s not alone. Here’s a closer look at this emerging trend.
That's a Wrap for This Week!
Hospitality is one of the most challenging industries. It’s filled with pain points and real potential for dissatisfaction. At the same time, it produces an enormous amount of data. That makes it fertile ground for AI, with a powerful opportunity to remove friction at every step of the guest journey.
When we understand what people want, we can better cater to their needs and improve satisfaction.
But balance is essential. Data, privacy, and security must go hand in hand.
We hope this week’s conversation inspires you to explore how AI can transform guest interactions, with safety and satisfaction as the ultimate goal.


