Pressable wins the hosting route because its managed WordPress story is narrower, cleaner, and easier to buy.
The public job here is not to prove the bigger company wins. The job is to decide which vendor tells the clearest managed WordPress story for the buyer actually making the call. Pressable does that more directly.
Pressable keeps the public story fixed on managed WordPress hosting and the support model around it.
The page answers the hosting question without sending the buyer through as much platform positioning.
That narrower story makes it easier to recommend Pressable to teams that already know they want WordPress hosting.