Throughout the first season, and especially in the last two episodes of season one "A Secret Kept From All The Rest" and "O, Mouse!" we see The Crows, and Jacob in particular, act as an antagonistic Inspector Javert towards Batwoman due to distrusting vigilantes. This is a trope seen time and time again in fiction, and is most likely quite reminiscent of Quentin Lance's distrust of The Hood/The Arrow in the first few seasons of Arrow. Except, when you really think about it, there's a key difference: The Crows aren't the police, even if they constantly act like they are. They are a private security firm, and as stated in "O, Mouse!", Batwoman's work is done for free. Thus, there's a good chance that Jacob's real reason for disliking Batwoman is because she helps people for free, thus effectively muscling in on their Punch-Clock Hero business system, and acting as a rival to them. While public officials like Quentin Lance and other typical examples of the Inspector Javert archetype have valid reasons for hating vigilantes that align with their personal moral code, Jacob may well just be motivated by profit.