I recently purchased software to the tune of ~AUD$25k, where downloading and installing a trial version makes almost no sense given the target audience: laser cutter, where each model of machine from any specific manufacturer can have a slightly different dialect of G-Code, and this type of software is often way too complicated for the average operator to nut.
So I sent a couple of emails and got swift responses and screen-sharing demos from both companies I contacted.
The sorts of programs I can download a trial version of and have running in half an our or so are nowhere near as mature as the products we short listed.
So I'm going to suggest it depends a lot on the target audience. When you're handing over multiple tens of thousands for a semi-bespoke software package management, in my experience, typically require interaction with a sales agent. This is in the context of physical industry, I can't speak for the software world, where perhaps spending multiple tends of thousands on online services is common? I have no idea.
It all depends on the product. Once you start getting into niche products which cost thousands or tens of thousands per year to use, the assumption is that the customer is a serious business with funding that has a known problem to solve. There will be a much smaller number of approaches than with a cheap consumer facing product and a conversion is worth a lot, so it makes sense to pair prospective customers with a domain specialist / sales person immediately to tailor the pitch to the specific candidate, modify the solution as necessary to fit the customer's needs, and make sure they are happy.
