This source/speakers match is a very interesting and complicated subject by itself.
Matching doesn't mean efforts to literally directly compensate, it usually requires a lot of thought and experimentation. It is easy to completely screw up the sound, to throw it in disarray. But I would guess that, generally speaking, your choice of table/arm/cartridge/phono stage should not be too different than your choice of speakers. The idea is to make the speakers sound their best, not to make the speakers sound the way they don't really want to sound.
So, in the end the source might be more important but you choose speakers first and upgrade them last. At least, that's how I see it.
I bought my modest speakers 25 years ago but the sound that I have now is light years away from what it was. Everything else was upgraded.