Gillespie Smith has worked as an urban planner across the nation to create walkable, safe and resilient communities. Prior to working with Friends of The Underline, she served as the Sr. Manager of Planning, Transportation and Resilience for the Miami Downtown Development Authority.

She also led Neat Streets Miami where she created the Miami Dade Complete Streets Guidelines and kickstarted a downtown bicycle network. As the manager of Million Trees Miami she created the Growing Green Bus Stops and the Street Tree Match Grant programs, empowering communities to deploy green infrastructure to combat extreme heat.