Little Nest Preschools

Jessica Castleberry

Jessica Castleberry has always been drawn to teaching starting at the age of five when she was planning activities and performances for her younger siblings.  They called her “bossy”, but Jessica simply considered herself highly creative with a clear vision.  By age nine she was babysitting and organizing her friends for appointments and     sending them out with a babysitting kit she created.  Little did she realize that one day she would own the only specialized daycare facility in Rapid City.      

After a few jobs and some college classes, Jessica became a stay-at-home mother.    During this time for over a decade, Jessica found time to teach preschoolers specialized classes in art, music, dance, yoga and drama classes for organizations     such as the Dahl Arts Center, Black Hills Community Theatre, the Academy of  Dance Arts, Storybook Island Children's Theatre, and the Rapid City School Systems, among others.  She also started Meadowlark Productions where Jessica wrote and produced children’s plays and taught many more acting classes.  With this production company, Jessica was able to dabble with the first idea of a preschool of fine arts which planted the seed for many things to come. 

With unexpected changes in her life, Jessica went back to school and finished her degree, became the artistic director of Storybook Island Children’s Theatre, a vocal instructor for Haggerty’s Musicworks and a preschool instructor for the Douglas   School District. When the entrepreneurial bug hit her, Jessica took the plunge and opened Little Nest Preschool out of her home in 2010 with four students.  Within four years, she moved into her first commercial site and in 2017, she opened an additional location, Little Nest Preschool South.  Currently, the preschools serve 87 families and employ 18 early childhood educators and other staff members.       

Jessica is dedicated to mentorship, professional recognition for early childhood educators and raising the bar for early childhood education in the state of South Dakota.   She is a conference presenter, author of Preschool Curriculum for $10 or Less and a preschool music songwriter.  In addition to her National Child Development Associate credential, Jessica also holds a Director Certificate and is a graduate of the 2015 SD CEO Women in Leadership series from Black Hills State University.  Jessica was awarded the SD CEO Young Enterprising Entrepreneur of the Year Award in 2016. She was also selected for and graduated from the Leadership Rapid City Class of 2016 and is a 2017 alumna of the Goldman Sachs 10,000 Small Business program.

Jessica has a commitment to the community of Rapid City. She is the head of the committee for the Rapid City Early Childhood Educator of the Year Award, and serves on the committee for Live Well Black Hills and the Campaign for Grade Level Reading. She also serves on the Board of Directors for the South Dakota Association of Child Care Directors, the Early Childhood Care and Education Network and is the president of the South Dakota Association for the Education of Young Children.

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