Bailey’s career trajectory reflects her passion for the outdoors, significantly shaping her life. Bailey began her career as a Region Manager for the Chicago Park District from 2001 to 2003. In this position, she led the strategic planning and operations of parks and recreation centers in Chicago. She oversaw a team of thirteen staff members engaged in recreation, facility management, and landscape operations. She also managed an operating budget of $20 million.

After 2003, Bailey assumed the Manager of Parks & Recreation position for the City and County of Denver, Colorado. She continued to lead strategic planning and operations, but this time for Denver’s Parks and Recreation department. In addition to overseeing the department’s maintenance, she worked alongside city leaders to aid with acquiring land, developing programs, and planning initiatives.

In 2008, Bailey transitioned from working for cities to Vice President of Centers and Strategic Planning for Outward Bound. This nonprofit educational organization is a leader in providing outdoor active learning expeditions for people of all ages, including students. Outward Bound strives to be inclusive of Black, Indigenous, and People of Color (BIPOC) in outdoor settings and aims for their expeditions to develop character and leadership skills in their diverse participants. In almost four years with Outward Bound, Bailey grew the nonprofit’s presence from two urban locations to six. By bringing her skills and experience from previous employments, Bailey led the way in development efforts and increased revenue by $1 million. Additionally, she established consistency in Outward Bound’s evaluations and best practices in outreach and community development.

Following her impactful time with Outward Bound, Bailey became a part-time Project Consultant for GreenPlay, LLC in 2011. In this capacity, Bailey organized consultant teams to provide the necessary services for agencies working in parks, recreation, and open spaces. Bailey continued as a consultant until early 2023.

Bailey brought her significant experience fostering inclusive outdoor spaces when she founded Youth Outside in 2014. Since then, as President and CEO, Bailey has been leading the organization in managing their grantmaking portfolio to shift resources to underserved communities, directing their training and capacity-building programs to develop future BIPOC leaders, and leading advocacy work to promote racial justice in outdoor and environmental movements. In 2021, the organization changed its name to Justice Outside to reflect its growth and work serving people of all ages and providing equitable access to the outdoors. At the heart of Justice Outside is the goal of strengthening relationships between BIPOC individuals, therefore nurturing bonds within these communities and with the natural world. Bailey sees her organization as working towards dismantling structural barriers between BIPOC and outdoor spaces.

Bailey strives towards achieving racial justice in outdoor and environmental spaces through other means. She serves on the Board of Directors for the Environmental Grantmakers Association, the Children & Nature Network, the North American Association for Environmental Education, and the Blue Sky Funders Forum.

In addition to her leadership of Justice Outside, Bailey Co-Chairs the Bay Area’s Environmental Education Funders Collaborative and serves on the Environmental Literacy Steering Committee for the state of California. Outside work, Bailey enjoys yoga, being outdoors, and spending time with her loved ones.