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Why, When, and How to Upgrade Your Hospitality Software

Why, When, and How to Upgrade Your Hospitality Software


To manage big change, answer the critical questions

A while back, a prospective TravelNet Solutions client remarked that he would rather “take out his liver with a spoon” than change his PMS software again.

Maybe you can relate. Anyone who’s been in the hospitality industry a while probably has a horror story or three to share about a particularly disruptive and stressful software migration.

It goes something like this: We had a system, and maybe it didn’t work well, but it worked. We vetted all the vendors and made a decision that not everyone agreed with. Promises were made and expectations set. But implementation was a nightmare, training was inadequate, and everything broke. Our initial optimism gave way to despair, then anger, then a rare accord — that we must never change software again.

Sound familiar?


Why change a working system?

If it ain’t broke, don’t fix it. We all know the saying. The question of whether something is broken or not is a matter of fact. Whether it’s working as well as it could is speculative. The point being, nothing makes you second-guess a big change like a new tool that doesn’t immediately meet your expectations.

Even so, technology and competition pull us along, sometimes forcibly, toward change. And time after time, we hope for a dramatic improvement that requires very little from us, only to be disappointed that it’s not just our processes and systems that have to change. It’s us. The older we get, the harder that becomes.

Change happens in the gap between where we are and where we want to be. The smaller that gap, the harder it is to justify a disruption. Many hospitality pros are still enjoying their best revenue year ever, which makes that gap seem very small. But is it really?

The crucial question is whether strong performance came as a result of your current systems and processes or in spite of them.


When success is a red flag

A big revenue year is actually a perfect time to reflect. Some key questions to ask yourself:

  1. To what extent did we create these results?
    If your performance was a direct or indirect result of a concerted effort, congratulations! You earned your success. Maybe you made capital improvements, ran some strong marketing campaigns, or hired additional staff. But if you can’t connect the dots between your results and your efforts, they should be taken with a grain of salt, which leads us to …
  2. Are they repeatable?
    When market conditions favored or practically guaranteed success, as they did in 2021, ask yourself if it was an outlier or part of a stable trend. Sometimes a region just becomes a hot destination, in which case you may have entered a new normal. Look at the broader economic context for clues. If you had an up year, there’s a good chance everyone else did, too. If you grow without gaining market share, you probably left money on the table.
  3. How did we scale?
    This is a big one. How did you manage the uptick? Did it make you feel overwhelmed and understaffed, or empowered? A busier than usual year tends to expose cracks in your operations that should be sealed before it happens again.
  4. What does this success mean for us?
    If record revenues mainly helped you catch up, then you should look at how you got behind. Was it staffing? Expensive debt? Likewise, if you find yourself with more working capital than usual, maybe now’s the time to invest it.


When your software is holding you back

Most of our clients come to us not because systems and processes are broken, or even because they had a down year. It’s because they have a sense that they could or should be doing better. Maybe the system doesn’t do something you want, or your current vendor is ghosting you. There are lots of good reasons to gripe about software.

The sense of “wrongness” about your software can be a hard impulse to act upon because the numbers may not support it. If revenue is growing year over year and owners are happy, a gut feeling doesn’t seem like much to go on, especially considering how disruptive a software change can be. Still, if you know your market and think you ought to have a bigger slice of the pie, you’re probably right.

So how do you know if your hospitality software is holding you back?


  1. Overwhelm.
    If busy stretches leave you and your staff stressed and irritated, consider whether the tools you use all day, every day require too many steps or convoluted workarounds. Modern software such as Track uses triggers and automations to simplify routine tasks and seamless integrations that don’t require any heavy lifting from you. Even something that saves just ten minutes per day adds up to 40+ hours per year per person.
  2. Proprietary technology.
    Hospitality is one of the last bastions of proprietary tech. Software built on the modern cloud is standards-based and device-agnostic, freeing you from old ecosystems designed to lock you in. If you have your own migration horror story, there’s a good chance proprietary software was involved.
  3. Time since the last upgrade.
    If it’s been five-plus years since you overhauled your software, you’re probably missing out on a ton of cloud-based computing benefits that would help out your business, such as improved security, hassle-free updates, clean integrations, easy configurability, and of course, triggers and automations that work while you sleep. Hardware hasn’t changed all that much in the last several years, but software has seen some major shifts.
  4. How many windows do people have open?
    If your staff immediately logs into ten or even twenty different systems to start their day, you’ve got a problem. Modern software like Track eliminates the need for “unitaskers” that ask too much of employees, especially sales agents. You’d be amazed how much a unified solution can do without requiring additional software.
  5. High and/or fast turnover.
    The current hiring environment is hard enough without making new hires learn clunky software — especially if they’ve grown up with cloud computing. Dragging your employees back to 2010 is a quick way to lose them. If you’d describe your onboarding process as a “long ramp,” it might be time to modernize.


When to upgrade

There are two whens involved with an upgrade: When it becomes necessary, and when you should actually begin the process. Getting either of these wrong can lead to a poor experience, so let’s look at them in greater depth.


When is it time?

Not everyone is ready to change their PMS or CRM. If cash flow is shaky or you’ve just experienced some churn, like a managerial shakeup, you may want to wait until things have leveled out before upgrading. Nothing is more stressful than compounding changes.

Software is a major investment, so consider whether that money is already earmarked for something else. If you’ve already made a plan, it might be wise to stick to it and plan your upgrade for a later time.

It’s hard to know when it’s time to pull the trigger, but there are a few warning signs you shouldn’t ignore, all of which contribute to hidden costs:


  • It feels like you can’t afford to scale. If it doesn’t seem practical to grow without adding staff, it may be a sign that your systems and processes are already stretched to their limits. We have had more than one Property Manager who, before adopting Track, had made the difficult decision to stop bringing on new units because they felt their software was holding them back from scaling effectively.
  • Your system is like a game of whack-a-mole. Workarounds that “make” a system work for you add complexity, and complexity costs money.
  • High attrition, especially for new hires. If it’s hard to retain good employees in general, especially new hires, your system might be too hard to learn. Plus, when only a few key people know it well, they can feel put upon or simply leave and take that knowledge with them.


Chances are, any costs you identify as a result of operational problems and inefficiencies are just the tip of the iceberg. Software is no longer merely a tool. It has become the glue that holds hospitality operations together. There always comes a point when you can’t just squeeze another year out of your solution. Only you can know when that is.


When should it happen?

Not surprisingly, most migrations take place during the low season. But it’s not just your schedule you need to worry about. Software implementation teams are likely at their busiest when you’re at your slowest. That means striking a balance, which is why you should consider the shoulder seasons to implement. Regardless, we recommend initiating the process at least seven to nine months before you want to go live on new software. The right software transition will not be quick! If someone tells you can do this within a short period of time, run!

As with any complex project, planning ahead and pecking away at the prep work is the best way to avoid the hair-on-fire scenario that so many hospitality pros have come to associate with a software migration. Do yourself and your staff a favor and bake the prep work, such as auditing, into your regular activities — even when you’re busy “minding the store.”


How to manage a migration

Because a major software change is so important — and potentially disruptive — you should strongly consider appointing one person whose job it is to project-manage the process. This way, the time of year may not matter as much.

No matter how big or capable your shop is, nobody is going to think they have the time and expertise to take point on something like this. Clearing somebody’s plate is only going to put more stress on those who have to pick up their slack, and that’s a recipe for attrition.

One Track client created a technology coordinator position to manage not only the implementation itself but the vetting process as well, which took them well over a year. Evaluating vendors raises dozens, if not hundreds of questions and concerns that the vendor needs time to address. Having a single, dedicated point of contact simplifies matters for both you and the vendor, further minimizing potential disruptions or surprises when the time comes to flip the switch.

If you can’t hire a dedicated coordinator, know that something is going to have to give. Adding the job to somebody’s plate means their regular duties must change. Be ready to listen to their concerns, and be prepared to compromise.


Forming a committee

Ideally, you should also put a committee together to audit your current situation, clearly articulate your wants and needs, and make critical decisions with respect to the big change you’re planning to make.

The committee should comprise key stakeholders, including and especially people who are in your PMS, CRM, or call center software on a regular basis. It doesn’t have to be big, but it should include people in the front and back offices. Don’t fall into the trap of only having management at the table. In fact, the less management you have, the more honesty you might get. The thing they’re hesitant to mention might be the feature that unlocks your team’s full potential.

Let’s face it, the days of executives making big decisions alone are all but over. Shared governance is a fact of modern business. There’s too much at stake, and the people who hold the stakes need to be heard.

We cannot stress enough the importance of a functionally diverse committee in this decision-making process. Your people will spend more time in the software you’re buying than they will on Facebook or TikTok. They need to be part of the process, or you’ll invest in the wrong product.


Vet your vendors

If you’re under the impression that all solution providers will expertly shepherd you through the migration process, and that it mainly comes down to the software and the price, you might be in for an unpleasant surprise.

Software migration is fraught on both sides of the equation, no matter how sound the planning. You’re going to be on the phone, email, or chat a lot. Like, a lot. Things go awry. Key understandings are missed. You and your vendor are going to need each other, but you, the customer, will expect and deserve highly responsive service after the sale.

Ask your vendor about their support policies and tools. Ask about response times. Most importantly, ask what they spend each year on improving their migration experience and after-sale support. To date, TravelNet Solutions has invested more than $25 million in research and development. That’s part of a long-term growth strategy and not a short-term profits and consolidation strategy.

Finally, look carefully at the company leadership, structure, and funding. How experienced are they? What’s their posture toward innovation and customer feedback? What mechanisms are in place to build upon and improve their offering?


In Summary

Software migration horror stories abound, but such tales are slowly edging into myth. Standards-based software hosted in the modern cloud has taken a lot of the guesswork and hassle out of the implementation, but as noted earlier, problems can and will arise. Good software should adapt to you, not the other way around. Don’t settle for software that doesn’t have the flexibility to do what you need it to.

And definitely trust your gut when it comes to support. A capable, available, and responsive support team represents a huge investment that newer companies simply can’t afford to make. But without adequate support, even the best software can become practically useless.

Remember, a new vendor may have a deep understanding of your industry but know little or nothing about your particular operation and its quirks. The more involved they are in the end-to-end migration process, the better they will come to understand your specific needs and limitations, which is key to a smooth transition.

Change is hard, but it’s the only path to growth. Chances are, software migration has come a very, very long way since you last invested in new hospitality software. If you’re haunted by the ghosts of implementations past, take a closer look. Fear of disruption shouldn’t keep you from pushing your business to new heights.

If you have 50+ units under management and would like a free analysis and demo to see how Track could work for you, give us a shout. You’ll be glad you did.



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