Based in Harlem, Chesray’s work focuses on the intersection of storytelling and transformative arts and cultural initiatives that seek to humanize and center marginalized communities. She worked with some of New York City’s top art education institutions, such as the Theater Development Fund, St. Ann's Warehouse, The Dream Center in Harlem and Urban Arts Partnership. Currently, Chesray serves as Co-chair of the Taskforce on Equity and Inclusion for the New York City Arts in Education Roundtable. Most recently, Chesray served as Director of Theatre at Harlem School of the Arts. She also worked in maximum correctional facilities in New York State with Rehabilitation Through the Arts as their program manager and Curriculum specialist. Chesray also worked for the International Theatre Project as their Director where they devised and toured original theatre in South Africa.

Chesray holds a B.A. in Community Psychology and Sociology and an Honors in Social Development and Policy from the University of Western Cape, South Africa and a M.P.A. in Public & Nonprofit Management & Policy from New York University.