I was massively underpaid in one of my past jobs, when I found out I just asked for a 25% pay rise, I didn't have another offer back then but was approached by recruiters. Then my boss gave me a 30% pay rise, make me realise I was even more underpaid than I thought, so after that I ask for pay rise every year and get it most of the time.

I didn't have the baggage you have, but if you like your job, ask for a pay rise, if they like you equally, you'll get it, it doesn't always come with a better annual review. Meanwhile prepare to leave for a better company.

a fintech company in nyc, bloomberg? :)