If, for example, you put something in the cart that costs $1.79, he will figure out that $1.79 is closer to $2.00 than to $1.00. He will show that as $2.00, and make 2 marks on his page.
Then you put something in the cart that costs $2.49. That is closer to $2.00 than to $3.00, so he will make 2 more marks.
Then you buy something that costs 99¢; that is very close to $1.00, so he’ll make another mark, but the fifth mark goes sideways. Every $5.00 you put in the cart will result in a mark like this.

The next dollar you spend starts another set of marks.

As you go along, he can count the crossed lines by 5’s to give you a running total. When you get to the cashier, you both will see how close his estimate was.

Older kids can pay and check the change.