I don't know if they were the first but I think of 37signals and Basecamp as the ones that first nailed the multi-column/highlighted plan form of design that has become so dominant.
Here's 2009: https://web.archive.org/web/20090307125843/http://www.baseca...
if you go back to 2007 you can see the same structure in a plainer presentation; it's easy to see how they went from one to the other: https://web.archive.org/web/20070831191822/http://www.baseca...
Pretty interesting!
Also interesting: they list their plans, from left to right, from most expensive to least expensive (and their current plan pages do the same). I feel like that's rare? I can't remember the last pricing page I've seen that lists it that way, aside from these. All the ones I can (dimly) recall start with the cheapest (or free) option on the left.
… and neither Hey nor Basecamp (both from 37Signals) use that layout style anymore.
https://www.hey.com/pricing/
https://basecamp.com/pricing
huh, to me they look really, really similar, just a little more emphasis/direction on the basecamp page and a simpler set of offerings with more details each for hey.com.