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Anyone who has worked in municipal systems has probably dealt with the horrific web of systems that is Tyler technologies. Most others have never heard of them. But they have massive inroads in municipalities. Many, many USA cities use them to drive things such as court records, water billing, hr, payroll, etc. They’re a silent behemoth.
Out of interest - do you see a way for a competitor to come and eat their lunch in any areas?
The data-export problem is key. Tyler has no interest in helping you get historical data out of "their" system.
I've been thinking, recently, that the various state/local/fed govts should have to eat their own dog-food: there should be a govt API that is: (1) publicly available; and, (2) the only legal way to access data and make changes (when I'm feeling frustrated, this includes criminal consequences for govt employees that circumvent the system).

Want to get a new well? You can add a well-review task to the queue just as easily as a govt epmloyee. Want to know when your well request will get reviewed? The queue is available.

This is true. Other companies in this space spend a lot of time writing import routines for the old system's data.

Also, the other companies in this space suck too, for most of the same reasons.

Not entirely true. Acquisitions they've made in the past few years are focused on making data easier to access by the public.
Making data more available to the public is not the same as making it easy to import into a new system.
There's always opportunity. However: the space is, to be frank, kind of boring (mostly just CRUD apps) and has to deal with the government procurement process. Which is why I think no one has come up against Tyler yet. I'm sure someone determined enough could easily eat their lunch but most disruptor types aren't in the municipal CRUD app business.

Municipalities operate about 20 years behind everyone else. For example: asking for AI to determine when grass needs to be cut in medians is just unrealistic when most municipalities don't have the expertise or budget to even produce a functioning mobile platform for their base website.

I disagree with the sibling comment about the data export problem. I worked for a city and getting data in and out, while a hassle, isn't really too tough. Tyler and many other vendors are very lazy with their protections (as clearly evidenced by subject line) and with a bit of know how even very early on in my career I had no issues getting the keys to the city.

You hit the nail on the head- when I used to work for Tyler, the thing that stood out to me was how ingrained they were in so many government systems. Their software isn't great, but they have the momentum of already having sold and been installed everywhere. It's a lot easier for a government agency to increase the spending on a contract with an existing vendor than it is to find a new vendor.
To elaborate on your comment, which is absolutely 100% true, new vendors that require a certain amount of spend (basically any tech company selling you a decent sized system that does anything transactional is probably going to fall under this) usually require the municipality performing an RFP and it's a months long process to implement that and it requires a bunch of approvals up the chain. It's a pain for everyone involved, both the vendor and the bureaucrats in charge of selection. Once a vendor like Tyler that does everything is in, getting a new system from them is instead usually little more than a line item in the budget.
I question the assumption that Tyler made these systems intentionally difficult to use. I may or may not have been previously employed by Tyler (not working on Odyssey or anything adjacent to it) and can tell you that a majority of the software that they run is pretty much a stitched together amalgam of ancient, barely maintained systems that they got through acquisitions of other companies. Seriously, go look at how many acquisitions Tyler goes through in a year.

Most of these systems were probably made when you were still using dial-up. I'd guess that a majority of them aren't even supposed to be used through the web but through proprietary desktop software. Any website that you can access the data through was slapped on top of what was already there. It's kind of a miracle that you can get at this data at all without having to write a FOIA request and wait weeks for it to be mailed to you.

Another thing to keep in mind is that while Tyler deals with a lot of data that's "public" (in that it's paid for by tax dollars) the main customer for most of their software is not the public itself, but the government employees that use it. They know that this is a problem and I'd like to say that they're working on making it easier to access, but I don't know for sure since the company is absolutely MASSIVE. Way bigger than you'd ever imagine.

Not trying to defend the fact that this data was hard to get at, just hoping to maybe give some context. Data should be free and easily accessible to all.

Makes sense. Nice clean URLs are still not found in many places and it's just laziness, not malice, in almost every case.
How does that address the captchas?
Could be a performance thing. If a database is stressed and you are unwilling/unable to scale or optimize it, you can use a captcha to cut automated traffic.
All of these are government systems and as such have a lot of "Security Theater" baked into the software for compliance reasons. Any Tyler product has to abide by at probably half a dozen compliance codes and complex laws, such as captchas where they don't need to be.

This is also a big reason why it's so hard for a lot of this software to be improved quickly. Almost every change requires a long and drawn out approval process with various government agencies.