As Chief of Staff, Rachel Chewakin supports United to Learn to advance its mission, brand, and programs by driving strategy, accelerating cross-team collaboration, and bringing big-picture initiatives to life. She believes that lasting change in education is only possible when we center community voices, build strong systems of support, and create the conditions for those closest to the work to lead with confidence and clarity.

Her commitment to systems-level change is rooted in her early experience as a classroom teacher, where she witnessed both the brilliance of her students and the structural barriers they faced. That perspective continues to fuel her work—ensuring that educators, families, and school communities are supported through partnerships that endure.

Over the past decade, Rachel has held roles across school systems, nonprofits, and talent-focused initiatives in both Dallas and Chicago—including serving as Chief of Staff at The Chicago Public Education Fund and Director of Strategic Initiatives at the Principal Impact Collaborative. Across each role, her focus has remained clear: build trust, strengthen collaboration, and move from ideas to action, all with a goal of working toward a future where every student has what they need to thrive.

Rachel holds degrees from Arizona State University and Loyola University Chicago. She is a proud alumna of Teach For America DFW, Leadership ISD and the Urban Leadership Fellowship. Deeply committed to service, she currently serves on the Congregation Council for King of Glory Lutheran Church and is an active leader within the Junior League of Dallas.

Outside of work and community leadership, Rachel finds joy in spending time with her husband, Christopher, visiting new outdoor trails and parks, and exploring local spots in their Oak Cliff neighborhood.