Our industry is a resilient one. We have managed to bounce back from a multitude of financial and health-related catastrophes over the past century. However, the latest crisis brought a huge push forward in the adoption of new (or new to the hotel industry) technology. Some of this was for the safety of guests and some was for the cost-cutting initiatives made necessary by the pandemic. 
With each of these investments, brands, owners and management companies likely went through a relatively thorough evaluation process. Once the decision was made, an implementation process was created followed by a training process. Some savvy hoteliers may have put in some type of monitoring program to track usage but the ones that added a return-on-investment tracking process will be the ones to come out ahead. 
For many, this is where things stopped. Very few (if any) companies invest in ongoing support beyond the basics of keeping the software up and running. Many individual hotels and their staff were left to wander the path of ongoing usage, thinking they knew the full extent of the software's capabilities. 
If you doubt this, look at your existing technology, then ask yourself, "Who is the expert in it?" or "Who in your organization is responsible for keeping up with new releases, enhancements, training, ongoing usage?" Chances are there is no one.
The fact is the farther removed from implementation the more diluted usage becomes. The initial users after implementation are typically trained on all aspects of a product. Then as new users are brought onboard, they are taught the pieces the original user used, while the unused features (even though they might be quite valuable) are ignored or forgotten.
Run this through multiple generations of user training (think about the turnover rate in the hospitality industry) and by generation three or four, the typical user knows just enough to do his or her job and nothing more. Now add in the enhancements and new features the typical software-as-a-service vendor adds in a year, and you get a system where users utilize a small percentage of its actual functionality.
This means the next salesperson with a slick sales pitch can unseat an existing vendor easily because no one knows what their actual technology can do for them. "Can" is the important word in the sentence. The reality is that while you may think you know what your technology is doing for your current users, you likely don't know what it could do if only you had kept up with the technology and the vendor.
This begs the question: Who is responsible for this process? Should the purchasing company be responsible? Should the vendor be responsible? The answer lies somewhere in between. 
What's Missing from Your Evaluation Process?
Let's start with how most companies evaluate a new technology. A quick Google search will result in 10 to 15 checklists on how to evaluate most technology. Additionally, depending on the sophistication of the company writing the check, there may be someone in-house who has a checklist specific to his or her previous experiences. Typically, the following things are evaluated at varying degrees of complexity:
Disaster recovery: Testing, frequency of testing, recovery time and geo-redundancy are a few of the categories in these. This makes sense because everyone wants to make sure their data won't be lost because of vendor errors.
Security: PCI compliance, audits, firewalls, log file management, identity management and visibility into emerging threats are all reviewed to exhaustion. Again, this makes sense because the protection of personal data is paramount.
Flexibility of service ecosystem: Typically this is limited to the system's ability to integrate with other systems. No one wants a rigid system where they can't cross-pollinate data.
Service-level agreements: This is almost always focused on uptime. Uptime is important but SLAs should cover much more.
Global reach: This is the one often dropped when the company doesn't have (or doesn't believe it has) global reach.
Costs: Setup, maintenance, license, et.al. are included for obvious reasons. 
Features: Do the existing features answer the pain points of the organization? This should be done but does the evaluator have a clear understanding of new pain points that may occur if current users aren't utilizing all the functionality of the existing product?
Word of mouth: Typically this is limited to the "references" provided by the vendor. 
This is by no means a complete list, but it highlights the top items evaluated. Do you notice anything missing from this list? The one thing rarely evaluated is the training partnership component. How does the vendor partner with your company to facilitate ongoing learning? What about ongoing updates? Is your staff up to speed on the latest, perhaps essential, changes to the software?
Most software vendors have some version of a learning-management system that houses all their intellectual knowledge about the product.