Category: Special Features

A Property Management System (PMS) is the software that runs your hotel — reservations, check-in, housekeeping, billing. A Point of Sale system (POS) handles your food and beverage operations. Together, they are the technological backbone of your property. Migrating to new versions of both simultaneously is one of the most complex projects a hospitality operations leader can face, but a necessary one if you’re using outdated software.

You may think you’re ready for the task. You may love technology, have managed big projects before, and feel confident going in, but don’t underestimate the toll it the upgrade can take. Here are the lessons I’d want someone to share with me before starting this process.

(If you’re early in your career, this may not apply to you. This week’s post is a slight departure from the usual leadership advice, but feel free to file this one away for the future.)

Choose the Right Vendor

There are many vendors in this space. On the PMS side, well known options include Oracle Opera, Mews, and Agilysys Versa. For POS, you’ll find Oracle Simphony, Toast, and Infogenesis among the most widely used. Do your research, talk to peers in the industry, and request demos before making any decisions.

One thing worth considering before you even get to vendor selection is ecosystem. Many properties piece together several best-in-class SaaS products — a PMS from one company, a POS from another, a reservation system from a third — all connected through integrations. On paper it sounds flexible, but in practice it means multiple support centers, additional implementation costs, more stakeholders to manage, and integrations that don’t always talk to each other as seamlessly as advertised. When something breaks, and something will break, you’ll spend valuable time figuring out whose problem it is.

An enterprise provider that offers a full suite of products under one roof is usually a more expensive upfront investment, but the operational benefits are significant. One support team, one relationship, one system that’s built to work together.

Whatever you choose, the quality of your vendor relationship will define your experience. The right partner shows up when things get hard. At the Agilysys Inspire user conference, CEO Ramesh Srinivasan opens the conference by putting his personal cell phone number on the screen in front of the entire audience. His message is simple: if you’re not getting the support you need through the proper channels, call me directly. That is the standard you should hold your vendor to. Choose wisely.

Timing is Everything

Timing is everything with a project of this magnitude. Begin planning as far in advance as possible — ideally six months or more before your target go-live date. Every property has a slower season, and some are fortunate enough to have a full closure. Whatever your situation, identify the window of least resistance and protect it.

Installing critical software when the house is full is a recipe for disaster. A slower period or closure allows for thorough testing in a low-risk environment, dedicated training time for all staff members, and minimal impact on the guest experience. The more runway you give yourself, the better positioned you’ll be when go-live day arrives.

Prepare Yourself and Prepare Everyone

Once you have a date for the install, communicate it immediately to all staff, especially department leaders, then communicate it again. A project of this scope has a long lead time and people need regular reminders as the date approaches. Ensure everyone knows what is happening, what the expectations are, and what their role in the process will be.

For hourly employees this may simply mean limiting time-off requests so they can attend training. For leaders it could mean lengthy preparation to ensure all data is accurately migrated from one system to the next. Having a shared calendar or project timeline is a huge help, which brings us to…

Organize and Analyze

There are so many moving pieces with a project of this magnitude. It is imperative that project stakeholders stay organized and not be intimidated by the tasks ahead or the obstacles that pop up along the way. Keep your to do list open at all times as you will be constantly adding to it and, hopefully, crossing things off. Some tasks are more important than others and it is helpful to identify which ones are a critical need and which can be addressed later. Time is your most valuable resource on a project like this, so spend it wisely.

Have a Support Network

No leader can do this alone, no matter how strong they are. During the install process, there will be a team of vendor trainers and engineers who are there to assist in implementation, training, and problem solving — they do this for a living and, when given the opportunity to do so, will really shine and help tremendously. What does that opportunity look like? Here is an example: a POS trainer arrives with a detailed preparation list of tasks to accomplish prior to his arrival. One item on that list is to prepare a training space and install all of the POS terminals for the team to use. Many properties fail to accomplish this and the first day of a trainer being on site is essentially wasted on this time consuming task. Don’t be that property.

Support also comes from other stakeholders. Your IT department is HUGE and needs to be heavily involved in this entire process. If you do not have their buy-in, the project will fail. Other important stakeholders are the departments that use the software daily — think F&B, front desk, reservations. A POS install is next to impossible without the input and guidance of real world users. This is usually a restaurant manager, but it doesn’t always have to be. Sometimes the most valuable person in the room is a tech savvy line level employee with years of experience.

Change Management is Never Easy

Really this is what it all boils down to. People get so used to the way they are currently doing things, especially if they’ve been doing it for many years, that the thought of change is scary and unwelcome. Leaders need to be prepared to explain why the changes are happening, what the benefits are, and what the obstacles will be along the way. Everyone needs to understand that challenges are inevitable and that their leaders and vendor are committed to overcoming them. There is light at the end of the tunnel.

The reasons for undertaking a project like this vary — outdated technology, a growing property, new ownership, or simply the need to meet the expectations of the modern traveler. Whatever the reason, your team deserves to understand it. When people know the why, they are far more likely to embrace the how.

Post Implementation

Go-live day is not the finish line, but it is a critical milestone worth celebrating. Once the install is complete and the dust begins to settle, the real work of refinement begins. Staff will discover things that need fixing, workflows that need adjusting, and features that aren’t configured quite right. This is normal. Expect it and plan for it.

Keep the feedback loop open. Your team on the floor are the best source of information about what is and isn’t working so create a clear channel for that feedback to reach the project manager. Vendors like Agilysys invest heavily in product development and rely on customer feedback to improve. Hotel leaders bear the responsibility to outline exactly what those improvements should be. Your voice matters more than you think.

The weeks and months following a successful migration should show steady improvement. If you have done the work outlined above, your operation will be in a better place than it was before, and it will keep getting better. These projects are daunting, but if you’re facing one, trust the process, lean on your team, and know that your operation will be better for it.

In June of 2025, my wife and I travelled with our then 1 year old son Henryk to Poland. It was his second flight ever and his first international flight. Like many parents, we were nervous – nervous that he wouldn’t sleep, would cry the whole time and of course that we would be those passengers that disturbed others.

As our journey began, KLM provided exceptional service and our son thankfully rested in solace. Our flight attendant was efficient in her job duties but more importantly, she was genuine in her approach and care. She made eye contact, smiled and of course asked about Henryk. Where were we headed? How old was he? Had he flown before?

When she learned it was his first international flight, she smiled and disappeared for a moment. She came back with something we didn’t expect: a little baby flight kit.

Inside was a children’s eye mask, a kids bag tag, a coloring kit, and a handwritten note congratulating Henryk on his first international journey.

It was such a small thing and likely cost KLM a few dollars. Operationally, it took the flight attendant maybe three minutes of her shift, but in that moment we felt the magic of true hospitality. Our family felt seen, heard and that we mattered. The flight attendant helped turned what could have been a stressful flight into something special and memorable. Henryk still has his little baby kit and we still have the note. He’s not quite old enough to color just yet, but when he is, rest assured we will use it!

Scalable Intimacy

Will Guidara calls this “scalable intimacy” in his book Unreasonable Hospitality. It’s the art of creating personalized, memorable moments – at scale.

At his restaurant Eleven Madison Park, they had a “hangover kit” for guests who looked a little worse for wear the morning after. At KLM, they have baby flight kits for little travelers, and maybe even other gifts for different occasions. KLM has probably given out thousands of these kits on flights around the world. But it was the first time we received it, and I can only imagine we were among the many who felt a bit of magic from this moment.

What Hospitality Leaders Can Learn

So what can hotel and restaurant leaders take from this?

Ask questions and listen closely. That flight attendant could have just served drinks and moved on. Instead, she asked about Henryk. She learned our story, listened closely and identified an opportunity for authentic hospitality. Train your team to be curious about guests – not intrusive, but genuinely interested. The questions unlock the opportunity, but you must listen to identify it.

Build systems for intimacy. You don’t need to invent something personal for every guest. Create repeatable moments that feel personal. First-time guests. Anniversary dinners. Business travelers who’ve stayed 10+ nights. Families with young children. Build the system, then train your team to recognize the moment.

Small gestures, big impact. That kit probably cost KLM $5, but the loyalty it created was priceless. My wife and I are already planning another trip. We’re flying KLM. Not because they have the cheapest fares or the most convenient schedule, but because a flight attendant took three minutes to make our son’s first international flight special.

The best hospitality doesn’t always require grand gestures. Sometimes it’s just noticing – and showing someone you noticed.

Hi – I’m Vincent. I used to go by Vinny until my first role in sales when several guests on the phone would say “BENNY?!?” or “DENNY?!?”. I’ve been in hospitality all my life, starting at the age of 16 when I took my first job at Kmart (yes retail is hospitality!), but my first hotel job was as a Valet during my senior year at Penn State University. At the time I was parking nice cars, meeting famous people and bringing home pockets full of cash – what more could you ask for? This was 2010, and for the past 15 years I have had the pleasure of working at some incredible hotels and, more importantly, the opportunity to work for some incredible leaders. They, along with some dedicated trainers (shoutout Christine and Cindy) have taught me a lot about this wonderful industry and what it means to be a leader.

I’m not an expert, but I do feel I have something to offer by now, and thus I have created this blog, The Practical Hotelier. My goal is simple – to help new and emerging leaders succeed in their field. My focus will mostly be on real and applicable lessons based on either my own experiences or those I’ve gleaned from a book, podcast or another leader. Some will be short snippets and others will be longer deep dives.

The bar for success is low—if I can teach one person something new, I will have succeeded. I firmly believe we are in the golden age of hospitality. People are drowning in technology and craving an authentic human connection. Unfortunately, many staff lack the skills needed to provide the service and connection our guests desire.

Furthermore, hospitality has for many years been seen as an “unglamorous” profession, much like electricians and plumbers in the last 10 years. Look at them now—they’re in high demand and commanding impressive salaries. Hospitality professionals are in a similar boat—we have high demand for (quality) labor but not enough supply. The job of a hospitality leader is more important than ever, and we have two imperative purposes.

1. To serve our guests

As Will Guidara says in his incredible book Unreasonable Hospitality: “The moment you start to pursue service through the lens of hospitality, you understand there’s nobility in it. We may not be saving people’s lives, but we do have the ability to make their lives better by creating a magical world they can escape to—and I see that not as an opportunity, but as a responsibility, and a reason for pride.” That mindset and belief is what gets me through the long hard days. We truly can create magic and it should be our North Star.

2. To serve our team.

We also have a responsibility to teach our staff, both young and old, that this industry can be a glorious and rewarding profession. You can travel the world, meet interesting people and make a great living. Yes, the hours can be challenging, especially early in your career, but great leadership can change that. When leaders prioritize work/life balance, inspiration, and purpose, they create an environment where people want to stay and grow. We need to ensure the talent pool continues to grow and prosper so our industry can thrive in its golden age.

Why did I choose a blog instead of a podcast like everyone else in 2025? Well, the written word and the ability to communicate with it is becoming an increasingly rare and powerful thing. In general, I would like to encourage more reading and will recommend plenty of leadership books on this platform. Selfishly, I also want to flex my own creative muscles through writing.

I’d like to end this first post with something I encourage everyone to start their day with – gratitude. Thank you for taking time out of your day to read this. I believe there is immense value in always being a student of leadership – any time learning is time well spent. See you next week!