The head of my DD's primary school (500+ children) always seems to know all their names and what's going on in their lives.
She makes a point of being on the door for things like first/last day of term and always attends every individual class play, special assembly etc.
When we went to view the school, she took DD & I round 1-2-1, then did the same again the following week when we went for a second look. She does this for everyone as 'it's too important a decision to not do it that way.'
She follows all the children's academic progress and gets involved with giving them little rewards i.e. they go to her office and choose from a 'lucky dip' box when they reach certain reading targets. The 'prize' itself doesn't matter so much imo, but the children know that the head is taking an interest as well as their own teacher which seems to be a real boost.
On the couple of occasions I have had to pick DD up because she's been poorly, the head has been around and aware of what's going on and around for a chat.
When I had a few queries in the first year (DD's reception teacher was not so hot!) she was quick to see me and never made me feel like I was being unreasonable/overprotective/wasting her time.
I know through work that she does get the backs up of some other local educational bods - but I get the impression it's because she is very focussed on doing what is right for 'her' school, which (selfishly) works for me tbh!