Jessica is a lifetime resident of District 35. She attended Rapid Valley Elementary School (where she served as student council president in the 5th grade), Dakota Middle School, and graduated from Rapid City Central High School.

After working as a preschool instructor for a local school district, Jessica decided to open Little Nest Preschool out of her home in 2010.

Little Nest Preschool LLC has now grown to three commercial locations in Rapid City, with 33 employees and over 150 students.  Jessica has been awarded the SD CEO Young Enterprising Entrepreneur of the Year Award (2016) and the Small Business Administrations South Dakota Woman Owned Small Business of the Year Award (2018). Jessica is also a graduate of the SD CEO Women in Leadership Program (2015), Leadership Rapid City (2016), and Leadership SD (2020), and is an alumni of the elite Goldman Sachs 10,000 Small Businesses Program (2017).

Political career

Jessica first became involved in politics as an advocate for quality early learning experiences.  She served on the board of directors for the Child Care Directors of South Dakota and was President of the South Dakota Association for the Education of Young Children 2017-2019. In this role, Jessica wrote and received grants for the organization, led statewide stakeholder events, travelled to Washington DC numerous times to meet with legislators, and became a national conference presenter for professionalism in early childhood education. Jessica also testified as a proponent for bills in Pierre, worked with legislators on bills, facilitated several public policy panels throughout the state of South Dakota, and was featured three times as an early learning expert and advocate on South Dakota Public Broadcasting. Jessica has also worked very closely with Rapid City Mayor Allender’s office on his early learning community initiative, and helped form the framework for Early Learner SD and Early Learner Rapid City. December 31st, 2019, Jessica was appointed by Governor Kristi Noem to fulfill the South Dakota State Senate term of Lyndi DiSanto for District 35.

Jessica is committed to the community of District 35 and the State of South Dakota. She is a Christian, a Republican, a Constitutionalist, a fiscal conservative, a small business owner, and a proud mom to three wonderful teenagers. She is thrilled to have this opportunity to represent her community and neighbors that she loves.

Jessica, Student Council President

Rapid Valley Elementary School, 1994

Jessica, Graduate Leadership Rapid City Class of 2016


Jessica, Advocating in Washington DC 2017, 2018, 2019


Jessica, Awarded Small Business Administrations South Dakota Woman Owned Small Business of the Year 2018


Jessica, Graduate Leadership South Dakota Class of 2020


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Jessica Castleberry for SD Senate

1010 9th Street #14

Rapid City, SD 57701