Horrifically bad match-up for Jackie. If this is Servant Kiara, she has class advantage thanks to Alter Ego typing.
>Horrifically bad
Only if you take FGO's type-matchup system as lore-canon, which means that assassins are better at taking down Dragons (Riders, mostly) than actual dragon slayers such as Sumanai (saber) and George (rider).
Very much going by gameplay mechanics with that comment. Lorewise, I'm still not sure how Jackie would fair. If I recall correctly, her NP's true form is a sort of curse, and I'm not sure how susceptible the Demonic Bodhisattva is to curses.