In a small bowl, mix cream cheese and ranch seasoning until fully combined.
Lay the slices of ham out in a single layer on a clean surface. Pat each slice dry with a paper towel.
Spread the cream cheese mixture evenly across each slice of ham, ensuring it reaches all the edges.
Pat the pickles dry with a paper towel and place one pickle at the edge of each cream cheese-covered ham slice.
Roll the ham tightly around each pickle, securing with toothpicks if necessary.
Slice the rolled ham and pickle into ¾-inch pieces, discarding the ends if desired. Arrange the pieces on a plate or platter.
Cover with plastic wrap and refrigerate until ready to serve.