Jessica Schilling brings over 20 years of experience in education, engaging students from diverse backgrounds. Before transitioning to teaching in 2004, she built a strong leadership foundation by managing sales floors in Wisconsin and Illinois. With a background of working in both urban and suburban schools, she has committed her career to supporting at-risk children and those facing unique challenges.

Early in her career, Jessica led retail teams through new store openings and department initiatives, skills she continues to apply today. Her life-long love of figure skating also transformed into professional coaching over the years. However, her true calling is in teaching and education, work she began at Milwaukee Public Schools. As a Special Services Educator, she spent eight years ensuring students who were unable to attend school due to illness or injury could remain connected to their education through the city-wide Home and Hospital Instruction Program. She then became the Academic Lead for the Pregnant and Parenting Youth Program at James Madison and South Division High Schools. Jessica joined The Oasis Project as a volunteer tutor in 2016 and has since worked to address the unique challenges faced by economically disadvantaged children in affluent communities. As The Oasis Project grew rapidly, Jessica took on various roles assisting the Founder. In 2018, the Board of Directors officially hired her, and she now serves as Executive Director.

Jessica has repeatedly witnessed the power of a multidisciplinary approach in transforming the lives of children and their families. She firmly believes that every child, regardless of their circumstances, has important potential through their inherent gifts to share with the world. She is passionate about empowering students with the support and opportunities they need to achieve their brightest future.

Outside of work, Jessica enjoys substitute teaching in Special Education and volunteering in the community. In the warmer months, she and her family take road trips, exploring our National Parks.

Jessica is always delighted to connect and collaborate in support of children’s success. Reach out to her at jschilling@oasisprojectwi.org to learn about opportunities to get involved with The Oasis Project!