Drain the olives well in a strainer. Dry both sides of each ham slice you are going to use and lay them on a cutting board. I found it easy to lay down a double layer of paper towels, place two slices of ham near an edge and fold the paper towel over, pat dry then place on the cutting board.
Spread softened cream cheese on each ham slice. Right side is spread, starting left side, it is not a thick layer.
Add a row of olives on one side of each ham slice. Slice the ham into strips between each olive. I found a pasta cutter works wonders with this. (Yes, I ate the missing one on the left, and for the scrap piece on one side of the ham, I ate that too, I call that a pre-snack snack.)
Starting on the end with the olive, rollup each strip and secure with a toothpick. Place rollups in the fridge until ready to serve. (Yes, this was the second batch, first batch was only 7.)