Breastfeeding nipple pain 1 week and 4 days

B

My nipples are super painful when he latches and it is really hard for us to get a good latch on one side, though the lactation consultant seems to think his latch is fine. I've resorted to pumping on the more painful side to give my nipple a break, even though this makes me feel like I have failed 😭. I feel like I have tried everything and get so frustrated when we can't get a latch, especially at night. Does your little one have trouble latching on one side more then the other? Any good videos for getting a good latch?