Founder and Director

Jessica Pope Horak founded The Trails School in 2018 with a commitment to providing Chicago’s Near North Side with an early childhood program that welcomes, values and nurtures young children from all backgrounds, giving them the foundation in their early years for a love of learning and school. A native Chicagoan who also grew up on the Near North Side, Jessica is thrilled to provide her community with a program that invests in its youngest community members and families.

Jessica previously worked as Assistant Director at Chicago’s Reggio-inspired Green Bean Day School & Nursery. Prior to earning an M.S. in Child Development with an Administration specialization from Erikson Institute, she worked as a tax and financial planning professional at PricewaterhouseCoopers. Jessica also earned an M.B.A. from the Drucker School of Management and a B.A. in Economics and Psychology from Claremont McKenna College.

She lives in Noble Square with her husband and young son, who is among the Trails School's first group of students!