[TheTaytay]

TL;DR: use a SaaS procurement vendor like TropicApp.io or Vendr.

Long version: First, my heart goes out to you. I was in charge of a lot of SaaS procurement for a number of years, and even as our company grew and our ability to pay went up, the lack of pricing transparency only became more frustrating to me! It used to be: “if we have to ask, we can’t afford it,” but then it became, “we can likely afford it, but it would be nice to make sure we should even talk to this vendor or industry before sitting through long eye-rolling sales calls.” (Or even worse, the 15 minute sales call with an intern to get you as a lead before you can talk to someone who knows anything.) but my blood pressure is rising, and I digress…

To level the playing field, we recently signed up with one of the “SaaS procurement” companies that has made this MUCH more tolerable. We use TropicApp.io, and have been happy with them and how they do business. They help us find and negotiate purchases. Even before we buy something, we can ask them stuff like, “we need a tool to do X. What are people using these days, and what is ballpark pricing and pricing model for a tool like that?” They (and their competitors) charge a percentage of the money they save you. They can’t help with smaller stuff (less than 5k per year), but are helpful with the rest. (Not affiliated with them or any competitors like Vendr.com - just happy that these companies exist now, and wish we’d found them sooner.)