Babysitter tips

Any moms who can give me tips on how to transition my son to a babysitter. Ok soooo I will be going to work first leaving at 4:45. Then my husband leaves at 7:45am so usually our son is still asleep till 8/9am. So if he stays asleep he will be waking up to the sitter...which i don’t know if it’s better for him to see my husband leave or if he’ll do fine waking up to her. Then I’ll be home by 2:30pm/3pm. Also she does have her own son around the same age that she will bring and he loves other kids soo I feel like he will be distracted with playing rather than thinking about me being gone. And yes I will be having her over several times before hand so he can get use to seeing her and stuff like that. But any other tips and tricks to help him transition?