Overcoming Challenges in Hotel Tech Adoption with Jacob Messina, CEO of Stayntouch
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Technology decisions scare hotel operators.
Pick the wrong PMS? You’re stuck for years.
Roll out the wrong system? Your team revolts.
Chase AI for the sake of AI? You lose the human touch.
In this episode of The Unchecked-In Podcast, TakeUp CEO Bobby Marhamat sits down with Jacob Messina, CEO of Stayntouch, to talk about what actually drives smart tech adoption in hospitality — and why most operators are solving the wrong problem.
Jacob has lived both sides of the industry. He started in restaurant kitchens (including a deli slicer incident that led to a day-one promotion), built his career at Loews Hotels and MCR in digital and performance leadership roles, and now leads one of the industry’s leading cloud-native PMS platforms.
This conversation is real, operator-focused, and refreshingly free of tech hype.
In This Episode, We Cover:
Why technology doesn’t fix broken operations
Automation scales structure — or chaos. If you don’t standardize first, tech won’t save you.
The biggest mistake operators make during system rollouts
It’s not the vendor. It’s change management.
How independent hotels outperform big brands
Flexibility. Personality. Empowered employees. Fewer rigid rules.
The 70/30 standardization rule
Standardize 70% of your operation. Focus your creativity on the other 30%.
AI in hospitality — without the hype
Use AI to increase efficiency and reduce friction. Don’t deploy it just to say you did.
Roadmapping the right way
Why Stayntouch locks in “untouchable” projects — and what operators can learn from that discipline.
The Big Takeaway
You shouldn’t start with, “What tech should I buy?” You should start with, “What am I trying to improve?”
Technology is an enabler.
Strategy comes first.
If you’re an independent owner, GM, or portfolio leader navigating tech decisions, AI conversations, or operational change — this episode will challenge how you think about adoption and control.
🎙️ Listen to the full episode of The Unchecked-In Podcast with Jacob Messina now.
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