Indeed, Josh works at HubSpot and the pricing page on our website preceded his joining. So, he shouldn't be blamed for it.
Having said that, HubSpot has spent a lot of time on designing our pricing model (vs. the pricing page).
For our first 2 years, HubSpot had a single price ($250/month). We've since run many, many pricing experiments and though the complexity bugs me sometimes, it's working.
But now that this thread is going, I think there are things we can do the improve the pricing page (even if we leave the pricing model the same).