[Cinnamon.]

It's definitely sketchy this person, who is so much older than you and has an important role at your job, is messaging you like this. You are still a minor, and you have every right to feel the way you do; everything you're thinking and feeling is valid. If you've been groomed before (as you've said) and you are having that same uncomfortable gut feeling, then I would let your parents know immediately or another trusted adult. And tell your work's HR department if there is one.