I think Krillin outmatches Kenpachi in strength, speed, toughness, and energy attacks.
I think Kenpachi outmatches Krillin in hair, Yachiru, and badassness
Still, Bleach gets up to city destroying levels of power, maybe a bit more hinted at. Kenpachi can't do wide-area destruction but he can fight with those who can just fine. DBZ has planet and moon destroying, and Krillin easily has the power to do destruction feats well above anything in Bleach by a lot.
Fought with the mini-Cells, sliced off 2nd Form Frieza's tail (even 1st form being a planet buster), took out multiple Saibamen each as strong as Raditz pretty easily (Raditz being more powerful than Piccolo by a ton, Piccolo being more powerful than King Piccolo by a ton, and King Piccolo being a city buster) before some of his large upgrades, and that sort of stuff.
Not any time he's vaguely active he hasn't. He got an upgrade from Guru, training from King Kai... he's one of the only two human characters who never really lets up on his training (Tien being the other).