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Funny anecdote: My mom prefers dull serrated knives. This is because she cuts ingredients over the stove and in her hands - she literally holds the tomatoes and diced them over the pot. A sharper knife doesn't enable this technique so she hates chefs knives.

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I also sometimes do this (although not with tomatoes). But my knife for this is very sharp and hook-shaped (I think the english word is "turning knife"). Only thing you have to pay attention to: when cutting "against your thumb", never press your thumb into the knife, otherwise things will get bloody. The technique that works best imho is to e.g. hold a carrot in one hand, knife in the other, thumb fixing the carrot and knife edge cutting in a rotating motion around the carrot's axis beside your thumb.

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