Here's what I've gathered:
So far as we know, all of the cephalopods seem to be venomous to their intended prey. As you pointed out, the beaks on smaller animals present a size limitation, but even some of the larger ones use a different technique: They use their radula -- essentially a tongue with rasp-like teeth -- to bore a small hole in a hard shell or exoskeleton. Then they can inject their venom/saliva into the victim.
The injection can accomplish multiple purposes: It immobilizes the victim (reducing the predator's exposure to injury), and in some cases actually dissolves the tissues involved. And especially for bivalves, it attacks the muscles holding the shells together allowing them to be opened.
While different species use variations on the theme, this arrangement seems pretty broad across the reef-dwelling octopuses, cuttlefish and nautiluses. The open-ocean predators like the Humboldt Squid and not usually going after hard-shelled prey; they can take bites of their victims — and do. The Patagonian Toothfish (we call it "Chilean Seabass" in the US) seems to be a favorite of the largest squid, and we have often retrieved half-fish with large chunks missing.
In each case, the chewing (apparently with the help of the toothed tongue) and swallowing is done very carefully, as cephalopods have the odd arrangement of having their esophagus-equivalent -- their throat -- passing through the middle of their brain.
When an octopus eats you, he has you in mind after the meal, literally.
There are reports that octopuses have been found dead from apparently a too-hasty meal; an urchin spine protruded from the gut into the brain, killing the animal that was in the process of devouring it. I used this as a minor plot point in one of the books I wrote in which the protagonists are evolved octopuses.
Young octopuses, even at the paralarva stage, seem willing to attack creatures of equivalent size, and there is a popular YouTube video of a Great Pacific Octopus attacking and killing (and subsequently eating much of) a shark that outmasses him by a good margin:
I apologize for the poisonous commercial and sappy narration. The situation is interesting, and it addresses your point, I think.
As for
Dosidicus gigas, the jumbo squid has been known to attack and kill others of similar size. One instance involved attaching a camera to the fin of one female, which put the watchers in the unhappy position of watching as this female was torn to pieces by other members of the shoal. That footage was featured on one of the recent cephalopod documentaries, but I don't recall which one. It was probably one focused on that species in particular.