The Winter Club Preschool is under the direction of Jillian Floriani. Jillian returned to the Winter Club in 2008 as a teacher in the Preschool. Jillian has a Master's Degree in Early Childhood Education from National-Louis University. 

Cindy Niesman returned to the Winter Club in 2005 after a hiatus spent raising children. Cindy has a Master's Degree in Early Childhood Education, years of experience in both public and private schools, and she previously taught here for seven years.